From Rooney to Ronaldo: Who are top deadline day summer transfers of all time?

Football’s summer transfer window is about to come to a close, with clubs across the world on the last-minute scramble to boost their squads.

Over the years, the last day of the summer window has seen teams make a number of important deals.

Here are some of the biggest deadline-day transfers to happen in the summer window:

Wayne Rooney: Everton to Man Utd, €39m (2004)

(FILES) In a file pictuer taken on March 4, 2013 Manchester United manager Alex Ferguson (R) and Manchester United’s English forward Wayne Rooney (L) attend a training session at the Carrington training complex.
| Photo Credit:
ANDREW YATES/AFP

Manchester United staved off interest from Chelsea to sign Wayne Rooney from Everton.

In 13 years at the club, Rooney won five Premier League titles, one FA Cup, three League Cups, the Champions League in 2008, the Europa League and a Club World Cup and remains the club’s highest goal-scorer with 253 goals.

Gareth Bale: Tottenham to Real Madrid, €101m (2013)

In 2013, Real Madrid dug deep into its pocket to secure Gareth Bale’s signature who was already making strides at Tottenham Hotspur.

Over nine years at the club, however, Bale struggled with several injuries. But his exploits in the final third saw the Welshman score over a century of goals for Real Madrid, including the stellar overhead kick against Liverpool in the Champions League final in 2018.

He left the club with five Champions League titles, four Club World Cups, three UEFA Super Cups, La Liga titles and as many Spanish Super Cups.

Ronaldo: Inter to Real Madrid, €46m (2002)

Ronaldo’s storming performance during the title-winning run in the 2002 World Cup made him the top priority for Real Madrid, which was putting together an array of star names, dubbed the Galacticos.

Real Madrid’s Brazilian Ronaldo poses with his trophies, the Golden Ball and The Best Player Fifa before Real Madrid’s Centennial match against a FIFA world side in Santiago Bernabeu Stadium of Madrid 18 December, 2002
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JAVIER SORIANO/AFP

Soon, the Brazilian switched from Inter Milan to Real Madrid on deadline day. He scored 104 goals in 177 games at the Spanish capital, winning two La Liga titles, one Intercontinental Cup and one Super Cup.

Mesut Ozil: Real Madrid to Arsenal, €50m (2013)

Mesut Ozil #10 of Arsenal celebrates his goal during the International Champions Cup match between Arsenal and Paris Saint Germain in 2018.
| Photo Credit:
THANANUWAT SRIRASANT

Mesut Ozil joined Arsenal for a then-club-record sum, becoming the most expensive German player at that time.

He won over the Gunners’ fans with his inventiveness and vision, and won the FA Cup in his first season – Arsenal’s first trophy in nine years. He scored 44 goals and assisted as many in 254 appearances for the London-based club.

Sergio Ramos: Sevilla to Real Madrid, €27m (2005)

Sergio Ramos of Real Madrid kisses the trophy after winning the UEFA Champions League Final match between Real Madrid and Club Atletico de Madrid.
| Photo Credit:
MATTHIAS HANGST/Getty Images

Sergio Ramos joined Real Madrid as the then-most expensive Spanish defender. He soon earned himself a legendary status at the club.

Ramos became one of the most decorated players of all time at the club, winning 22 major trophies, which included four Club World Cups, four Champions League titles and five La Liga titles.

Zlatan Ibrahimovic: Ajax to Juventus, €16m (2004)

Swedish striker Zlatan Ibrahimovic made a high-profile switch in 2004, when he moved clubs from Ajax to Juventus.

Ibrahimovic spent two seasons with Juventus, scoring 23 goals from 73 games. He would then shift allegiance to Inter Milan following Juventus’ relegation in the aftermath of the Calciopoli scandal.

Ashley Cole: Arsenal to Chelsea, €7.4m+ (2006)

Ashley Cole of Chelsea evades Steven Gerrard of Liverpool during the 2008 UEFA Champions League semifinal, first leg match between Chelsea and Liverpool.
| Photo Credit:
Jamie McDonald

Left back Ashley Cole was involved in a controversial transfer, moving from his boyhood club Arsenal to its London rival Chelsea.

Cole would go on to play a crucial role with Chelsea, winning multiple trophies, including multiple Premier Leagues and the Champions League in 2012. He is often regarded as one of the best left-backs in the history of the English league.

Claude Makelele: Real Madrid to Chelsea, €16m (2003)

Chelsea’s Claude Makelele celebrates winning the English Premier League after its match against Manchester United at Stamford Bridge in London, April 29, 2006.
| Photo Credit:
EDDIE KEOGH/REUTERS

After arriving from Real Madrid, Claude Makelele became the midfield conductor for Chelsea, under Jose Mourinho.

In the 2004/05 season, Makelele helped Chelsea win the Premier League title, conceding a competition-low of only 15 goals.

The France international Makelele made 144 appearances with Chelsea, winning two League Cups and the FA Cup, along with back-to-back Premier League titles.

Dimitar Berbatov: Tottenham Hotspur to Manchester United, €36m (2008)

Dimitar Berbatov moved to Manchester United from Tottenham Hotspur in 2008 after snubbing Manchester City.

Dimitar Berbatov of Manchester United celebrates with the Premier League trophy in the dressing room after the Barclays Premier League match between Manchester United and Arsenal at Old Trafford on May 16, 2009.
| Photo Credit:
JOHN PETERS

He then went onto help the Red Devils win two Premier League titles, the League Cup and the Club World Cup in his four seasons at Old Trafford.

Berbatov scored 20 goals in the 2010-11 Premier League season, sharing the League Golden Boot award with Manchester City’s Carlos Tevez.

Cristiano Ronaldo: Juventus to Man Utd, €15m (2021)

Cristiano Ronaldo made a sensational return to Manchester United from Juventus on deadline day in 2021.

Though, he failed to inspire United to silverware, Ronaldo made his mark with his finishing skills, scoring 27 goals from 54 appearances across two seasons.

Published on Sep 01, 2025