Arsenal winter transfer windows – Ranked worse to best | OneFootball

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.

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