Arsenal winter transfer windows – Ranked worse to best

(Photo by Catherine Ivill/Getty Images)
As many of you know, I like a list.

I’m sure many of you will be glued to Sky Sports News on Monday to see if Arsenal are able to get the attacker that even Arteta has admitted the squad needs. It’s fair to say our approach has divided opinion.

Some feel that it’s neglectful to leave any business to deadline day and that a striker arriving at the start of the month could have kept us in the FA Cup, had us closer to the top of the Prem, and not 2-0 down in the Carabao Cup. The window closes at 23:00.

To get you in the mood, I have ranked every winter window (since it became a thing) from worst to best. You might see why I get angry with our owners sometimes…

2016-2017

Has to be the bottom because this was the window where our transfer policy would finally catch up with us. Mr Wenger continued to be his employer’s shield, insisting Arsenal had money to spend but was only interested in a talent who would improve his squad and not wanting a signing for the sake of it. Some Gooners were starting not to trust his words. For the first time in nearly two decades, we failed to qualify for the Champions League.

2021-2022

Shamefully, for the second year running, players were paid to sit at home before having their contracts ripped up or loaned out while their deals expired, with the priority being to slash the wage bill. Mikel Arteta had got into the habit of washing his hands of talent the moment they didn’t suit his ethos instead of getting the best out of the resources he inherited. For consecutive January’s, a star player was given away for free. Many Gooners felt releasing Aubameyang was their manager sending a message to the dressing room, but in reality, the decision not to replace the striker would cost us a place in the top four.

2010-2011

This ranks low because a young team were top of the league in the New Year but clearly needed some experience, while the goalkeeper position was our weak link. We were not asking our board to pay over the odds or upset our self-sustained model. We simply needed an established goalie who was better than Almunia. Fulham offered us Schwarzer for £5 million, but we couldn’t budge on our £2 million valuation. That’s how tight we were, refusing to help the squad for the sake of saving a couple of million.

2007-2008

At this point, most Gooners trusted that a few years of limited investment in the squad would be worth it because, once the stadium debt was paid off, we would have an advantage by being a self-sustained model. We naively believed UEFA would follow their own FFP rules. This ranks low for giving up on Diarra way too soon. He would end up playing for Real Madrid. Could have been our Vieira replacement.

2015-2016

Frustrated by our failure to sign a first-team outfield player in the summer, there was a demand to help the team who were top of the league that January. When we only brought in Elneny, some Gooners started to lose patience with waiting for the stadium to be paid off.

Elneny
2014-2015

Another window where the disappointment was compounded by being top of the league but only strengthened by the arrival of Paulista. We also cancelled Coquelin’s loan from Charlton due to injuries in midfield. He would end the season starting in the FA Cup Final.

2002-2003

Like in the summer, the Champions seemed reluctant to spend. Matthew Upson made a loan move to Birmingham permanently. Had he stayed, injuries meant he probably would have started in the FA Cup Final.

2006-2007

First season at the Emirates, where it’s widely accepted that the club had limited funds to spend due to paying off the stadium debt. We did well to convince Portsmouth to give us money for Lauren, both parties playing down how bad his knees were.

2018-2019

Still discussed today, Unai Emery was not backed like Mikel Arteta would be. It would be made clear to the Spaniard that a Europa League squad were being paid Champions League salaries and the priority now was to slash the wage bill. At least the club were transparent with their fans, stressing they could only afford to consider loans. Denis Suarez was chosen simply as a body to fill up the squad, always injured.

2019-2020

In his first job as manager, Mikel Arteta had the same criteria to work with as Emery in his first window, despite Arsenal being in serious danger of not qualifying for Europe. Despite the Gunners being on course for their lowest league finish in a quarter of a century, we loaned Mari (with an obligation to buy) and Cedric (before he became a free agent). It felt like we picked these two because they didn’t cost an immediate fee rather than because we believed they could make us better.

2020-2021

I’m only not putting this lower because this was in the middle of COVID, which impacted the entire economy. With Arsenal playing in empty stadiums and not knowing when their customers could return, they lost serious revenue. Their handling of it, on and off the pitch, remains debatable to this current day. Mustafi, Sokratis, and Ozil were paid to rip up their contracts, Kolasinac and Maitland-Niles were loaned out to get them off the wage bill. For the third year running, we could only afford a loan deal. A certain Martin Odegaard.

2023-2024

Many felt we needed a striker if we wanted to make ground in the title race, evidenced by chances that Kai Havertz missed in the FA Cup. We were told behind the scenes that we were working hard to find someone, but only if they made us better. Things change, yet stay the same?

2013-2014

I often feel sorry for Kim Kallstrom when he’s described as one of our worst signings. It’s not the midfielder’s fault he was loaned while clearly injured. He only started once as a Gunner and made two sub appearances. Yet he contributed to our history by converting his penalty in our FA Cup semi-final, ending our trophy drought. Where, though, was the striker we had been looking for in the summer? (Sound familiar?)

2009-2010

Our limited resources were again made apparent when injuries meant we needed a centre-back. Our solution was to offer free agent Sol Campbell a short-term contract. He was only meant to be training with us as a favour from his former boss to help him stay fit. To be fair, the 37-year-old did well, to the point he felt he should have gone to the World Cup.

2012-2013

Van Persie had been sold that summer, meaning Gooners were now used to losing a star name every year. The fact we would do business with Man United left many questioning if the ambition was still to compete with them. Fans wanted the club to do something to show their intentions, so Monreal felt underwhelming, but he would actually be a solid servant for the club.

2004-2005

We gave Beveren £2 million for Eboué. The Belgian side was essentially our feeder club for five years. While we would play each other in friendlies, loan them talent, and invite some of their players for trials, Eboué was the only transfer. The relationship ended in 2006.

2011-12

Perhaps the one window I’m ranking high purely for nostalgic reasons. I was at the Emirates when Thierry Henry made his short-lived return. It was an honour just to see him come off the bench against Leeds, but when he scored, some people in the crowd were crying. In reality, though, we needed more than a short-term loan in what was one of our most difficult seasons since leaving Highbury. In the summer, we had sold Fabregas and Nasri and still would not reinvest all the money, as promised.

2017-2018

For better or worse, one of our most eventful winters. Out of fear of a fan backlash for again letting their best talent go to the Etihad, the club had decided they would rather let Sanchez run down his contract if it meant he took them back into the top 4 and brought in Champions League revenue. Mr Wenger assumed the Chilean would stay professional in the final year of his deal. When that wasn’t the case, a swap deal with Mkhitaryan seemed the best of a worst-case scenario. Breaking our record for Aubameyang (recouped slightly by offloading Giroud and Walcott) and Ozil extending his stay at the time felt like we had turned a negative month into a positive one. Let’s just say the Kroenkes would regret the salaries they agreed to.

2003-2004

Unlike Man United and now the richest club in the world, Chelsea, our summer investment had been limited. It was therefore a shock when we suddenly broke our transfer record for Jose Antonio Reyes. Arsène Wenger saw this as an opportunity to give the Spaniard some time to settle into a new culture. He had a memorable debut, scoring twice in the FA Cup against Chelsea. The only Invincible no longer with us.

2005-2006

This is when the transition truly gets underway in terms of breaking up the Invincibles for younger talent. Adebayor and Diaby get to experience the last few months of Highbury, but mostly, they are being prepared for the move to the Emirates. As is Walcott, who, despite not playing a second for us that season, somehow goes to the World Cup at the age of 16!

2008-2009

You could argue our first exciting winter signing since January had its own exclusive window. This was the season Man City got bought, meaning Arsenal were struggling to compete based on their self-sustained model. Arshavin had lit up the Euros, so Gooners waited in the snow for his purchase to be confirmed in the last seconds of deadline day.

2022-2023

Most of the month had been spent being told how Edu had agreed terms with Mykhailo Mudryk and Moisés Caicedo, telling Brighton not to price him out of a dream move to North London. Therefore, Trossard and Jorginho seemed like an anticlimax. It quickly became apparent, though, that we had got serious value for money, with the two still contributing.

Let me know your fave / least fave Winter Window
Dan Smith
Tags Winter transfer window

58 Comments

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  1. A highly-detailed article

    Aston Villa have Watkins/ Rogers and are signing Rashford/ Asensio/ Felix, while Arsenal just contacted Mathys Tel

    Maybe Arsenal don’t want to sign a new winger in the current transfer window

    I think Arsenal will surprise us with a new CF, despite the very little time left

    1. @Gai,
      My worry is having too much burden on Havertz to lead the line in all competition in last games of the season. He is no machine and he works a lot for the team. I can’t see how Arsenal will win a trophy this season with Havertz alone upfront,. May be Arteta should start trying Matinelli in the role?

      1. Havertz would likely get burned out since he has to press frequently

        Arteta said Nwaneri could play false-nine. I also feel Nwaneri could do hold-up play well due to his strength and low-center of gravity

  2. thanks for the summary. That was really interesting.

    I am hopeful for a surprise but if the math doesn’t work it is probably better not to waste the cash.

    I wondered if there was a serviceable attacker out there who could help but would not be a signature signing. Some of the people we moved were not first choice starters but could be decent extras when needed.

    Even when White and Saka return, we are still really thin, especially up front.

    As I said, thanks for this summary!

  3. Breaking News peeps –
    My sources have told me Tel his flying to London to talk to Spurs
    My sources tell me he wanted Arsenal and United but they only want a loan with no obligation to buy
    So he now has accepted Spurs
    I’ll let you know when I hear more lol.

    1. Romano and Ornstein said Spurs will also loan Tel with no obligation to buy

      I’m glad he’s heading to the toilet bowl, because he rarely used his weaker foot on his YouTube highlights, as compared to Martinelli and Garnacho

      All top EPL clubs have been signing new players in the current transfer window, except Arsenal, so we might see a panic buy in the last hours of the period

      Man City are signing an uncapped DM from Porto for £60m, but Arsenal are signing Zubimendi for merely £51m. I hope we’ll get that kind of high-profile signing soon

  4. It really hits you hard when you realise the ‘best’ winter transfer on this list is the one where we got Trossard and Jorginho. Jorginho was a magnificent player and Trossard is our very own Poundland Eden Hazard but it doesn’t exactly bring a tear to the eye when we look back at it.

    I like the idea of a self-sustainability model for the club and clearly Arteta fits right in with this ethos; the man could have all the money in the world and would still do his weekly shop out of the discount bin at Asda. But it has to be matched by ambition. And it isn’t.

  5. When you put five pass the champion on a canter, why make a panic buy in the Winter?

    With the big pretender well insight, no need to disrupt the chemistry at this delicate stage

      1. Oh Dan, does this five star performance tickle your memory of something.

        Remember the gaffer presentation in an interview to the Kroenke’s, where he explains home and European domination could come in phase five akin to Pool and the champions era.

        Not getting ahead of myself, but it seems the old guards have changed.

    1. My friend, is it a panic transfer if you take a striker even within a month’s time limit, when your two main strikers are injured? Or should you panic when You’re not taking anyone and you still have four months of the league and you’re in the knockout rounds of the Champions League? Are you Stan?

  6. Who is talking about panic buy? Just imagine any of martinelli, trossard or even harvetz getting injured now and we are left with no option except sterling to replace them. We need a stronger depth on the bench.

  7. 6 hours to go and no rumour of a player coming in!!!

    I guess Arteta and the board has given up on the season already and want to try again next week.

    This is pathetic and sad.

      1. It was definitely a PR stunt and there will be no second bid.

        The board and Arteta are playing with us and it’s not fair.

        We have to accept it now and see what the current players achieve by the end of the season.

        1. Title is lost today if we don’t do anything.
          Liverpool are counting down the hours
          Season is on life support and our owners have all the power to keep us alive and they won’t ….how anyone can defend them after this

  8. Since from the beginning it seems that they have no purpose for support, obviously because to do so they need…what a shame money….And where can we find it? The club is top in profitability, but if is to come out, then there are clamps … and the reasoning is that athletes really need money to come? We couldn’t even get Rashford, who had been heard of … now it crosses my mind that The guy may have completely lost his mind with the administration and left, otherwise if they were functioning properly, what’s the reason? Anyway, we wanted, we wanted, we wanted, many worthy candidates, but in the end, no one? Since You ask for support, but no one gives it to you. In my homeland, a proverb says, “He who does not want to ferment for thirty days is sifted.” We were once again overwhelmed by the nuts and in the end, nothing… Get out.And you’re ridiculously saying that Arsenal probably won’t make a single transfer in the January transfer window. Why do you want even two reinforcement transfers….fortunately, the kids seem to be coming out, Luis Skell And the nouveau riche, and very dynamically indeed

  9. Great article. It’s so interesting looking back at previous winter transfer windows.

    Winter transfer windows are notoriously tough to get quality players . I think we did well getting Trossard and Jorgino

  10. The striker at Ipswich Delap I think his name is. He looks like he’s got an eye for goal. Put him in a better team, and who knows what he could develop into.

    It doesn’t always have to be a player with a big name or reputation, sometimes it’s the smaller transfers that can surprise you.

    Anyone remember a certain Jamie Vardy, I believe he’s won a Premier League and an FA Cup. Just saying. 👍

  11. With the absence of Jesus and Saka. One can say our best team is what we put out on Sunday and demolished a poor Man city side.

    Hopefully we don’t have any other injury through out the season and the injured players return as fast as possible.

    Havertz.

    Trossard. Odegaard. Martinelli.

    Rice. Partey.

    Skelly. Gabriel. Saliba. Timber.

    Raya.

    SECOND TEAM –

    Havertz.

    Sterling. Odegaard. Nwaneri.

    Merino. Jorginho.

    Calafiori. Kiwior. White. Tomiyasu.

    Neto.

  12. Sky Sports News’ Gary Cotterill at the Emirates:

    “I’m told and it is my understanding that there will be no ins and no outs today at Arsenal and indeed in the whole of January.

    “No business, we understand, at Arsenal.”

    1. It has been looking increasingly unlikely as time has ticked away but at the beginning of the day, I thought the opposite. As a matter of interest, who were the strikers that were available this window that Arsenal have missed out on?

      1. Well no Sue I know what you will do
        But there were attacking players available who were either better or could have been another option
        We are so short

        And shame on anyone who defended that Watkins bid

        1. What will I do?
          It’s a fair question Dan and a shame that you haven’t stuck your neck out to name them. You refer to players being available but having read what Arteta said about this window, “a body” was not in the club’s plans- only a player that would improve the squad.
          Ollie Watkins was a so so suggestion and not worth the considerable investment. Imo it’s important to weigh up the difference the signing would make versus the cost and the long term benefit.

      2. SueP,

        I think we should have gone for Delap at Ipswich.
        He’s got a good eye for goal, and if he was in a better team with the chances they create he could really flourish.

        It doesn’t always have to be a big name player, sometimes its the smaller transfers that can surprise.

        Anyone remember a certain Jamie Vardy, I believe he went on to win a Premier League and an FA Cup. Just saying.😉👍

      3. Marmoush
        Rashford
        Tel
        Ascenecio
        Ganacho
        Duran
        Watkins ( apparently lol)
        Khvicha Kvaratskhelia ( beautiful player )
        Kolo Muani
        Cunha ( release clause )
        N Williams ( release clause )
        Ferguson
        Xavi Simmons
        Osimehan
        Felix
        Nkunku
        Gimenez

          1. All of them meet the criteria of either being a better finisher then Havertz
            Someone to compete with the front three or another option
            And all available this winter
            So this idea that Arsenal couldn’t find anyone is false

      4. You will find that people will make a lot of noise but won’t come out with any realistic names.
        There is a lot of intellectual dishonesty, at best, on the part of some fans.
        The truth is that whilst we would like to have a striker there are few that are proven and that we could be confident would make a big impact on the team. Such players would also cost a lot.

        1. Marmoush
          Rashford
          Tel
          Ascenecio
          Ganacho
          Duran
          Watkins ( apparently lol)
          Khvicha Kvaratskhelia ( beautiful player )
          Kolo Muani
          Cunha ( release clause )
          N Williams ( release clause )
          Ferguson
          Xavi Simmons
          Osimehan
          Felix
          Nkunku
          Gimenez

          1. Now let’s bring in our old friend “context”.

            Rashford, Ganacho, Ferguson, Felix, Nkunku, Asensio, Tel – what on earth are you smoking?

            Marmoush, Duran, Kvaratskhelia – some of them over priced, and will be on huge wages. Tough to compete.

            Watkins – Negotiations stopped after sensible opening bid, because Al-Nassr massively over bid for their second choice striker. No brainer that Villa immediately accepted the Al-Nassr deal.

            Simmons – Doesn’t play in the position we need strengthened.

            Williams, Kolo Muani – Having really poor seasons.

            Too many wingers in your list, when we need a striker.

            So now we are left with:
            Cunha, Osimhen, Gimenez

            Cunha – doesn’t make sense spending at least 60 million on player who probably won’t be a starter after the summer transfer, and also he’s too similar to Havertz, and Jesus. His fee would have a knock on effect as well come the summer.

            Osimhen – I don’t no what the deal with this guy is, but clearly there must be a reason why clubs are not wanting to sign him. Ending up in Turkey on loan is a massive red flag.

            Gimenez – Now at Milan, but didn’t cost them much. So he’s the only realistic option from your list for me that we should have gone for. I guess a lot of players from the Dutch league have flopped lately in the EPL, so maybe that was an issue? At the price, we should have looked at him though. Good option for me.

            Then we have the context of how the club now operates in the transfer window. We are very meticulous these days. No more panic buys, and the club has already shown that they’re willing to wait to get their preferred targets. This method has been hugely beneficial long-term! Doesn’t make sense to splash the cash now on a short-term option, which then effects what we can do in the summer.

            That all said, we need the context of this season also. We’re missing too many easy chances, we’ve had a huge injury crisis, and Havertz is our only option upfront now. Whether you like him or not, if he gets injured, we’re completely screwed!

            We can partly blame Arteta for the summer transfer, but this window is on the board. Arteta has dropped more than enough hints that we need at least one more attacker. The board have hung him and squad out to dry in my opinion. It’s a disgrace that we didn’t even bring in a loan option. I am not sure what the board expect from Arteta with the lack of forward options at his disposal?

            1. The fact he did t sign any forward options in the summer is on him in the first place ,he had 3-4 months last window to sort it out .
              His choice to start the season was the Havertz and Jesus as his forward pair .
              Or did the board leave him out to dry in the summer as well

        2. David the above list has quite a few names any better alternatives to King Kai. I ty it’s you who is not being realistic in your all out, ” stand by your man”, loyalty to whatever those above decide to pass doy on us. I’m also still dreaming of Liverpool having a St Tottenham breakdown, similar to Rodgers’ team a few years back but it is a desperate longshot based on us not getting any further injuries and Everton kick starting their rivals collapse tonight.

        3. “Such strikers would cost a lot” as if Arteta signings cost peanuts.

          You have been given a list care to spin it with your usual dishonest remarks?

          Good job Dan for shutting up this “who is available” nonsense, hopefully for good.

  13. Arsenal is always the “wisest” when it comes to January transfer window. They will always claim there is no one out there good enough this time to improve them, while their rivals are busy strengthening their squads in areas they need to. It is not as if they will do much during summer transfers. They keep saying let’s hope no injuries instead of doing the needful. If Kai gets injured, I don’t know what other options Arsenal has upfront.
    Even a club with 115 charges still has the courage to strengthen their squads in. It’s unfortunate.

  14. I imaging now that the Curriculum of our upcoming Sporting Director is totally blank ,Cero achievement, but full of experienced due to his
    immense initial work with this great Team.

    Thanks for the good work.

    M.Arteta

  15. “This ranks low for giving up on Diarra way too soon” – we didn’t give up on him, he thought he should have been an automatic starter, but he had to wait because flamini was ridiculously good that season, and when diarra did get a chance, he simply wasn’t as good – it was a very high bar to immediately come in and outshine flamini that year. The problem was flamini’s contract was also ending and I suppose we expected we’d convince him to sign on as he’d become a key player – it ended up blowing up in our face, but it was diarra’s (perhaps understandable) impatience that saw him leave so quickly, not our desire to push him out.

  16. Arsenal was supposed to balance the squad. How the window closed without a single signing is very disappointing. Every time when one player is injured it’s like four regular players are not in the team. Other teams are buying players over or under price, they buy to balance the squad. Arsenal since the signing of Rice, they will never want to buy any players. Arsenal sell their players very cheap and want other teams to do the same. Many teams that are not doing very well like Arsenal are selling their players at around 100 million. When did Arsenal sell a player for around 50 million, we hardly sell for 30 million and that must be a huge concern

  17. What has been proven once again is that the transfer correspondents are idiots and make a fool of themselves to make a living from their profession, and that Arteta He’s mocking us dryly, he’s the one who said before Jesus and Bukayo were even injured that we wanted at least one reinforcement….after they were injured it was deemed imperative, names were paraded equal to two Indexes….what else could the conclusion be…that maybe we are finally complete and no reinforcement was needed? This is paranoid in their own statements. Or maybe the line from the owners for Once again it was, what’s the point of spending when we’re doing better than everyone else financially, and that titles only matter to stupid blood-donating fans? What else can I assume, this mockery It lasted two months, and combined with the very cheap flights of the summer, I think the profit for the Kroenke family is dizzying… and you sit and chew on their words, saying It’s like you’re partners….For example, when a team is the injury champion to key players, he says he will buy purely for reinforcement, and that is the right thing to do, and he doesn’t do it, besides mockery, what other conclusion can be drawn? that the lyrics he may have I don’t even care, what is more pleasurable than even the lyrics of the titles is the pleasure of increasing profits…. So white, black, yellow, mixed, always continue to fill the Kroenke’s bank, otherwise known as Emirates Stadium, and you do everything you can inside and outside of it, with season tickets and everything else, to keep them in the loop, and you can see a title again when Your beards are turning white, and the elders of the upper world. We no longer hope rationally, but in miracles from God and such.

  18. I wonder where this window would fit in the list had this article been written today? I suspect, given the current needs of the squad, fairly highly!

    My thoughts are that the board has looked at the league, seen there is no realistic chance of winning it and pulled the plug on any further negotiations. Or maybe this is all down to Arteta’s arrogance. Who knows.

    Either way, I think we can look forward to seeing a lot more of Nwaneri before the end of the season and Havertz playing every minute of every game, which won’t annoy anyone on this site at all lol

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