Skip to content
GO TO bet365 Sports
  1. Football

Top 10 Summer Deadline Day Deals

The 2023 summer transfer window for English and Scottish clubs closes on Friday 1st September and several high-profile moves are likely to go down to the wire.

We have picked out 10 of the biggest transfers completed by Premier League clubs as the clock ticked down on deadline day.

Claude Makelele - Real Madrid to Chelsea, 2003

Chelsea pounced late in the summer of 2003 to bring France midfielder Claude Makelele from Real Madrid to Stamford Bridge.

Real star Zinedine Zidane was disappointed by his compatriot's departure and Makelele went on to play a crucial role in Chelsea's success under Jose Mourinho, anchoring the midfield superbly and winning back-to-back Premier League titles in 2004/05 and 2005/06.  

Wayne Rooney - Everton to Manchester United, 2004

Chelsea were eager to land 18-year-old Wayne Rooney on deadline day the following year but Sir Alex Ferguson, no mean judge of a young footballer, lured the Everton ace to Manchester United instead.

A fee of £27m for the talented teenager looked like something of a gamble but Rooney swiftly made himself at home at Old Trafford, scoring a Champions League hat-trick on his debut against Fenerbahce, and he left in 2017 as United's record goalscorer.   

Ashley Cole - Arsenal to Chelsea, 2006

England left-back Ashley Cole's acrimonious move to Chelsea dominated the headlines on deadline day in 2006.

A member of Arsenal's Invincibles team of 2003/04, Cole's switch to Stamford Bridge marked a changing of the guard in London and he established himself as a Chelsea legend, winning the Premier League, Champions League, Europa League, four FA Cups and one League Cup in his eight years with the Blues. 

Carlos Tevez - Corinthians to West Ham, 2006

Argentinian prospects Carlos Tevez and Javier Mascherano arrived at West Ham in a shock move late in the 2006 summer window and Tevez is fondly remembered by Hammers fans.

He scored the only goal against Manchester United at Old Trafford on the final day of the season, keeping West Ham in the Premier League at the expense of Sheffield United, and went on to star for United, Manchester City and Juventus. 

Dimitar Berbatov - Tottenham to Manchester United, 2008

Tottenham supporters have learned not to go to bed early on deadline day and Dimitar Berbatov's 2008 move to Manchester United is the first of four Spurs-related deals on this list.

The classy Bulgarian striker was a fans' favourite at White Hart Lane but a bid of more than £30m persuaded Tottenham to sell him to the Red Devils.

Berbatov joined Rooney and Tevez in a top-class attacking unit at Old Trafford, winning the Premier League in 2008/09 and 2010/11 and scoring 48 league goals in 108 appearances for United. 

Rafael van der Vaart - Real Madrid to Tottenham, 2010

Harry Redknapp is synonymous with transfer drama and the Tottenham boss pulled off a coup by signing Dutch playmaker Rafael van der Vaart from Real Madrid in 2010.

The midfielder had been heavily linked with Bayern Munich but, with just two hours remaining in the transfer window, Tottenham launched an £8m bid.

Van der Vaart settled in quickly, winning the Premier League Player of the Month award for October, and enjoyed two successful seasons in north London before returning to former club Hamburg. 

Hugo Lloris - Lyon to Tottenham, 2012

Tottenham's deadline-day business in 2012 included arranging a loan deal to Norwich for young striker Harry Kane and bringing in Lyon goalkeeper Hugo Lloris.

Both Kane and Lloris went on to enjoy glorious careers for the Lilywhites and the veteran keeper, who captained France to World Cup glory in 2018, is still at the club having racked up 127 clean sheets in 361 Premier League appearances.   

Mesut Ozil - Real Madrid to Arsenal, 2013

Arsenal left it very late to clinch a £42m deal for Germany playmaker Mesut Ozil, whose eye for a pass had been a major factor in Cristiano Ronaldo's prolific goalscoring record for Real Madrid.

Ozil didn't take long to demonstrate his creative prowess, setting up a goal for Olivier Giroud just 11 minutes into his debut at Sunderland, and he recorded 19 assists in the 2015/16 Premier League – just one shy of the record held by Thierry Henry and Kevin De Bruyne.     

Gareth Bale - Tottenham to Real Madrid, 2013

While one left-footed genius, Ozil, arrived in north London from Madrid in September 2013, another, Gareth Bale, headed in the opposite direction after Tottenham agreed a world-record fee of £85m with Real for the Welsh wizard.

Bale won three La Liga titles and five Champions Leagues during a remarkable nine-year spell at the Bernabeu, scoring a stunning overhead volley in the 2018 Champions League final against Liverpool.   

Manuel Akanji - Borussia Dortmund to Manchester City, 2022

Premier League clubs tend not to leave high-profile transfers until the last minute these days but Manchester City completed a smart piece of business on the final day of last year's transfer window.

Versatile Borussia Dortmund defender Manuel Akanji arrived at the Etihad Stadium on deadline day and, just over 10 months later, the Swiss stopper was celebrating his influential role in City's Premier League, FA Cup and Champions League treble.

Akanji played in the Citizens' 1-0 win over Inter Milan in the Champions League final and his stunning debut campaign has set a high standard for any 2023 deadline-day signings to match. 

Related Articles

bet365 uses cookies

We use cookies to deliver a better and more personalised service. For more information, see our Cookie Policy

New to bet365? Bet £10 & Get £30 in Free Bets Join Now

Min deposit requirement. Free Bets are paid as Bet Credits and are available for use upon settlement of qualifying bets. Min odds, bet and payment method exclusions apply. Returns exclude Bet Credits stake. Time limits and T&Cs apply.