Ranking Chelsea's 10 best transfer windows of the Premier League era | OneFootball

Chelsea are a club that notoriously spends a lot of money on recruiting players with mixed results over the years. Ever since Russian billionaire Roman Abramovich purchased the club in 2003, the Blues have ranked as one of the richest football clubs in the world and have invested heavily in their quest to attain domestic and European glory.

How the club have gone through managers over the years has made it difficult for a specific style of play to be established at the club. This has had the knock-on effect of players being bought to play a certain way under one manager which renders them less useful in a new manager's system.

In summary, Chelsea have made a lot of signings over the years which have not worked out. However, there have been windows throughout the Premier League era where they have got it right and the players signed have gone on to have long, successful careers at Stamford Bridge.

Here at GIVEMESPORT, we thought we'd rank the club's ten best transfer windows of the Premier League era. The transfer window was only introduced as a concept to the division in 2002, so no bits of business before that, such as the purchase of Gianfranco Zola or Frank Lampard, will be included.

Ranking Factors

This list has been compiled based on several factors:

Some signings on this list were great for the immediate future, but may not have been the best investment and meant the club only got a few years out of them before they were shipped out at a loss. There have been several occasions where Chelsea have definitely sold a player too soon so that will see the window lose marks, whereas if they managed to make a rare net profit over a window, that will boost its credentials on the list.

Additionally, individual signings will not always outweigh the business that goes alongside them. So for example, Michael Ballack on a free transfer in 2006 was a terrific signing, but the Blues also broke the British transfer record that summer to buy Andriy Shevchenko, who never kicked on in West London, so that window is not included in this list. So without further ado, let's dive in.

10 2023/24 summer window

We're going to give Todd Boehly the benefit of the doubt here and say the club got their business in the summer of 2023, right. The American has been, let's say, eager in the transfer market since buying the club, breaking all sorts of ludicrous records and already going over a £1bn spent purely on transfer fees.

Having appointed his fourth manager in just over a year in Mauricio Pochettino, the recruitment focused heavily on youth due to the Argentinian's reputation for developing young players, with Moises Caicedo, Christopher Nkunku, Cole Palmer and Nicolas Jackson representing some of the standout buys. The Blues also managed to offload no fewer than 14 first-team players, including a lot of ageing players on high wages.

9 2010/11 summer window

Chelsea's summer of 2010 was a lot quieter than the one before it on this list but still included several bits of good business. Ramires was the standout purchase, costing the Blues £18m, and serving the club for five-and-a-half years during which time he made over 250 appearances before leaving for China in a £25m deal in January 2016.

The West London outfit also bought young defender Tomas Kalas, who they would sell for a profit years later, as well as trading Joe Cole and £5.5m for Liverpool's Yossi Benayoun, which turned out to be not so great a deal as the midfielder only made 24 apperances in three years at the club. Other outgoings besides Cole included Ricardo Carvalho, Deco, Michael Ballack and Juliano Belletti.

8 2016/17 winter window

The window of January 2017 makes it into this top 10 mostly off the back of one transfer alone. Oscar was a talented young player, but when Chinese side Shanghai Port came calling with an absurd £60m offer, the Blues were in no position to turn it down and the Brazilian has remained in the Far East ever since.

In a window where they made no signings whatsoever, Chelsea were also able to shift John Obi Mikel, Branislav Ivanovic and Patrick Bamford off the wage bill, giving their side, which would go on to win the league title under the stewardship of Antonio Conte, a much more balanced look.

7 2014/15 summer window

This was a window that received a lot of praise at the time and had a lot of positive short-term impact, but the long-term consequences are what places this window in seventh place on this list. At the start of the second season of Jose Mourinho's second spell at Stamford Bridge, he made several big signings, including those of Diego Costa and Cesc Fabregas, who were both key players in the club's successful charge to the league title that campaign.

The hugely popular Didier Drogba also returned to the club on a free, but less successful were the purchases of Loic Remy and Filipe Luis, who between them only made 48 league appearances for the Blues. The most notable departure was that of Romelu Lukaku to Everton for just £28m and to indicate just how bad a decision that was, Chelsea would end up re-signing the Belgian for £97.5m in 2021.

6 2019/20 summer window

Chelsea were actually under a transfer embargo during the summer of 2019 and it says a lot that a window in which the club physically weren't allowed to sign players ranks so highly on this list. That's not completely true, the Blues were able to get around the ban somewhat as Mateo Kovacic's loan move from Real Madrid was made permanent as per Chelsea's obligation from the summer before, and the Croatian would prove to be an important player, making 221 appearances in his time at Stamford Bridge.

Aside from that minor loophole, the Blues had to contend with the loss of star player Eden Hazard to Los Blancos for £103.5m and they also decided to sell David Luiz to Arsenal for £7.83m. The club decided to focus their attention on youth players such as Tammy Abraham, Mason Mount, Reece James and Fikayo Tomori, making this window less about what Chelsea did do and more about what they didn't, or couldn't, do.

5 2011/12 summer window

The 2011 summer window involved multiple bits of good business for Chelsea, as they enjoyed particular success from their scouting in Belgium. Romelu Lukaku and Thibaut Courtois were two pick-ups from Anderlecht and Genk respectively and while it's already been mentioned how the forward's Chelsea career panned out, the goalkeeper would enjoy a successful career at Stamford Bridge, winning four major honours.

Juan Mata was the most expensive signing of the summer and he would enjoy two-and-a-half fruitful years with the Blues before joining Manchester United and earning Chelsea a healthy profit on the Spaniard. The surplus to requirements Yuri Zhirkov went back to Russia for £13.2 million while youngsters Michael Mancienne, Slobodan Rajkovic, and Gokhan Tore were also sold.

4 2011/12 winter window

Chelsea's luck in Belgium continued later that season as they picked up the talented Kevin de Bruyne from Genk for just £6.7m. Much has been made of the way the Blues dealt with the attacking midfielder, along with several other players of that era, but the fact is they were making a £12m profit on him just two years, and nine appearances, later, with the only downside being that it could have been so much more.

Gary Cahill was also an astute addition made that winter, with the centre-back signing from Bolton Wanderers for £7m and Patrick Bamford was also picked up from Nottingham Forest for £1m and would later be sold for six times that. Cahill's arrival spelt the end of Alex's time at Stamford Bridge, and he was offloaded to PSG for £4.2m while Nicolas Anelka left for China on a free.

3 2007/08 winter window

We move from one winter window to another and January 2008 saw Chelsea make several key additions to the team, which would reach the Champions League final later that season. 23-year-old defender Branislav Ivanovic was signed from Lokomotiv Moscow for just £9.7m and would go on to make 377 appearances during nine years at Stamford Bridge, winning every available trophy in that time.

Nicolas Anelka was also signed from Bolton Wanderers for £15m. Despite a slow start to his Chelsea career, in which he scored just once in his first fourteen appearances and missed the deciding penalty in the Champions League final shoot-out versus Man United, he would bounce back the following season, winning the Premier League Golden Boot with 19 goals and also won the league one year later.

In the early days of the Abramovich era, and before the introduction of Financial Fair Play, Chelsea used to spend money like it was going out of fashion, but things didn't quite work out how they'd hoped in the 2003/04 season. Under new manager Jose Mourinho in the summer of 2004 however, they got a lot right, bringing in several players who would go on to become Chelsea legends and help the club secure a first league title in 50 years that season.

Arriving from Marseille for £24m, Didier Drogba was the most expensive and he would go on to score 164 goals in 381 appearances during a total of nine years at the club, while Petr Cech was a bargain pick-up from Rennes and would go down as one of the greatest goalkeepers in Premier League history, with 494 Chelsea appearances to his name. Ricardo Carvalho, Arjen Robben and Paulo Ferreira were also good signings who would all leave a lasting impression at Stamford Bridge.

1 2012/13 summer window

Chelsea's best transfer window was almost indisputably in the summer of 2012, curiously coming just after the club had won their first-ever Champions League title against all odds. Eden Hazard was the standout signing as he left Lille for £32 million and the Belgian winger would go on to make over 352 appearances for the Blues, winning six major honours during his seven years at Stamford Bridge.

Oscar arrived from Internacional for £19.5m, which was three times less than what the West London outfit received for him four-and-a-half years down the line, and Marseille's Cesar Azpilicueta was also snapped up for just £7 million and would be a constant member of the Chelsea team for the next 11 years, making 508 appearances and being appointed captain in 2019. Victor Moses was also signed for £7 million, and he would play a major hand in the Blues' league title success in the 2016/17 campaign.