Eisha Acton
6 min readSep 8, 2021


This transfer window has been a crazy one. So many big names making big moves to big clubs and it has made for a very interesting summer. This got me thinking, this was such a big window, what other windows were this exciting? So, in this article I’m going to list my top 5 transfer windows of all time in no particular order. This series is brought to you by Kitbag — the worldwide leader for official football kits — do check out the link below to shop all their new season kits, they’ve just launched their Ronaldo number 7 shirts! I’ve left a discount code below soo happy shopping!


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First up, a big summer for transfers was in the 2001 2002 season when we saw Real Madrid break their transfer record. Perez raided Juventus for one of the best players around — Zinedine Zidane. They paid up £69.75m for the Frenchman and this transfer particularly paid off for Perez straight away, as Zidane scored one of the best ever Champions League goals. It was a volley against Bayer Leverkusen which ended up winning them the Champions League. They then went into the next season and won it again, with Zidane playing another key part in their success. Going to England and Manchester United also made some big moves, purchasing Juan Sebastian Veron from Lazio for £38.34m and Ruud Van Nistelrooy for £25.65m. Only one of these were actually successful and that was Van Nistelrooy, scoring 95 goals in 150 games, an amazing return while Veron couldn’t get going and just didn’t work for some reason so they decided to offload him to Chelsea two seasons later for a price of £19.62m, making a loss of £18.72m.


This was a standout window for two English clubs in particular — Manchester United and Chelsea. Let’s start with Man United as they only signed one player, Wayne Rooney. They signed the 18 year old from Everton for £33.3m, the second highest fee of this window and the rest, as they say, is history. He went on to become the highest goal scorer in Man United’s history, and in the process won 5 Premier Leagues, 1 Champions League, 1 Europa League and 1 FA Cup. Nothing short of a club legend. Speaking of club legends… that summer Chelsea also made the acquisition of one of their most legendary players; Didier Drogba. Jose Mourinho was told by Abrabmovich that he could get any striker he wanted and Jose asked for Drogba. Drogba was playing at Marseille in France. He just finished off a season where he scored 19 goals for Les Olympiens and Chelsea forked out £33.75m for the 26 year old. It was undoubtedly a masterclass signing by Mourinho, Drogba finished his Chelsea career with 104 goals in 254 starts, helping them win 3 Premier League titles, 1 Champions League and 1 League Cup. They also improved their defence by signing Ricardo Carvalo for £27m, Paulo Ferreira for £18m and Arjen Robben for £16.2m. This turned out to be worth it as they went on to win the league in back-to-back seasons.


Now let’s talk about the 2009/10 SUMMER TRANSFER WINDOW. This window was a memorable one for sure. The transfer record was broken by Real Madrid when they signed the one and only Cristiano Ronaldo from Manchester United for £84.6m but this wouldn’t be the only bit of business from Florentino Perez. He always goes big and that’s exactly what he did. He brought in Ronaldo but alongside him, he also signed Kaka for £60.3m from AC Milan, Karim Benzema for £31.5m from Lyon and Xabi Alonso for £31.05m from Liverpool. One significant departure from Real however was Arjen Robben being sold to Bayern Munich for £22.5m. Out of the top 6 transfers in that window, 4 of them were signed by Real Madrid amounting to over £207million pounds. The manager at the time Manuel Pellegrini, was definitely backed by Perez. They finished second in the league that season and crashed out to Lyon in the round of 16 in the Champions League. Pellegrini was sacked and Mourinho was brought in the prior season and he gave them a Copa Del Rey with the same core of players so all those transfers ultimately paid off.


Perhaps the most influential and historical transfer window in the history of football. The biggest transfer in history occurred during this window. Paris Saint Germain were looking to strengthen their squad and identified Neymar Jr from Barcelona as their ideal replacement. What happened next shocked the world. PSG paid his release clause, a mouthwatering £199.8m pounds. As you’ll remember, this one transfer had an immense impact on the football market resulting in inflation for every fee since. This move had a big domino effect and led to Barcelona needing to replace the Brazilian star and they did that with two big signings, Ousmane Dembélé from Dortmund for £121.5m and Philippe Coutinho from Liverpool also for £121.5m pounds. These signings did not work out for Barcelona but the money Liverpool got from the Coutinho sale was definitely reinvested into the squad wisely. They signed Virgil Van Dijk for £76.19m pounds in the following January window and he helped them to their first Champions League win in 14 years. It seems like the English and French clubs won this window while Barcelona were the losers of this one.


Lastly, let’s talk about this summer. One of the most high-profile windows in a while. Loads of stars making moves and the Premier League has definitely benefited the most out of this window, with lots of big names joining the league and making it one of the most exciting once again. Out of the top 3 transfers, all of them have moved to the Premier League:

  • Jack Grealish to Man City for £105.75m pounds
  • Romelu Lukaku to Chelsea for £103.5m
  • Jadon Sancho to Man United for £76.5m

Besides the fees, two the best players of the last 15 years have also sent shockwaves through the football world by signing to new clubs. Lionel Messi did the unthinkable and left Barcelona despite many thinking that he would retire there, the Blaugrana were simply unable to afford him due to their monumental debt. He made the switch to the French capital and signed for PSG, who may have enjoyed the best window out of any team. Their incomings read like this:

  • Lionel Messi
  • Sergio Ramos
  • Georginio Wijnaldum
  • Gianluigi Donnarumma on a free
  • Achraf Hakimi for £54m
  • Nuno Mendes for £35m

Whilst also managing to keep Kylian Mbappe!

As you know, Cristiano Ronaldo, also made a sensational return back home to Old Trafford from Juventus for a fee of £13.5m, after days of speculation that he may join Man City, Man United swooped in last minute to secure his signature. Man United also added Varane to their squad for £36m and this means that the commercial value of the Premier League has increased hugely thanks to all these superstars now playing in the league. I think that the Premier League is the winner of this year’s transfer window.

Well there you have it — the 5 craziest transfer windows, detailing the biggest figures, squad overhauls, club legends and big names doing the unthinkable and leaving their boyhood clubs. Have I missed any? Do comment below your thoughts! If you enjoyed reading — do applaud this article and follow me for more! Remember this series is brought to you by Kitbag, do check out the link below to shop all their new season kits, and use my code below for a discount:


Code: INTERNATIONAL [for 50% off]