Deadline Day has produced some of the most dramatic and unforgettable moments in the history of football’s transfers. These clubs sealed deals in the final hours that went on to shape entire seasons and eras of success. The closing of the transfer window often delivers iconic stories, stunning fans, and gears them up for the season ahead.
5. Cristiano Ronaldo: Juventus to Manchester United (2021)

- Transfer Fee: €15 million
- Position: Striker
- Nationality: Portugal
Cristiano Ronaldo announced his return to Old Trafford in 2021 under Ole Gunnar Solskjaer’s reign as Manchester United manager. The Portuguese striker scored a brace against Newcastle United following Peter Drury’s iconic rendition regarding the hero’s return.
However, Ronaldo’s return wasn’t as successful as he had hoped. Despite him scoring several goals in his second stint at the club, the club fell off its upward trajectory under Ole. Ronaldo was later axed from the squad under Erik Ten Hag and proceeded to record a controversial interview with Piers Morgan.
4. Mesut Ozil: Real Madrid to Arsenal (2013)

- Transfer Fee: €50 million
- Position: Attacking Midfielder
- Nationality: Germany
The German superstar joined for a then club record transfer fee, claiming his first assist on his debut at Sunderland. He brought an FA Cup back home to Arsenal in his first season at the club. There haven’t been many footballers more talented and creative than Mesut Ozil. In his 184 Premier League appearances for Arsenal, he’s scored 33 goals and produced 54 assists.
3. Ronaldo: Inter to Real Madrid (2002)
- Transfer Fee: €46 million
- Position: Striker
- Nationality: Brazil
Ronaldo, famously known now as R9, was at the very top of Real Madrid’s list because of the Brazilian striker’s iconic performances in the 2002 World Cup, bringing the trophy back home to Brazil. He was a part of Florentino Perez’s star-studded Real Madrid squad dubbed the Galacticos.
Ronaldo went on to score 104 goals and 34 assists in his 177 appearances for Real Madrid. He even won several accolades at the club and won the 2002 Ballon d’Or.
2. Gareth Bale: Tottenham to Real Madrid (2013)

- Transfer Fee: €101 million
- Position: Right Winger
- Nationality: Wales
Gareth Bale’s contributions to Real Madrid cannot be downplayed. Over his nine-year spell at the club, he scored 106 goals and registered 68 assists. He possessed a knack for delivering at the biggest stage and in the most important games, including an overhead kick against Liverpool in the Champions League final in 2018. He even won five Champions Leagues during this time. Despite his injuries and the controversy surrounding his exit from Real Madrid, he will be fondly remembered by the fans.
1. Wayne Rooney: Everton to Man Utd, €39m (2004)

- Transfer Fee: €39 million
- Position: Striker
- Nationality: England
Wayne Rooney’s move to Old Trafford away from his boyhood club Everton, meant he became the most expensive teenager in world football at the time. The hat-trick on his debut for the club in the Champions League against Fenerbahce was only a glimpse of what he had in store.
He finished his Manchester United career with 13 major trophies, including five Premier League titles, four League Cups and the Champions League, the FA Cup, the Europa League, and the FIFA Club World Cup once. He’s regarded by many as Manchester United’s greatest ever player and even overtook Sir Bobby Charlton to become the club’s leading scorer.
Conclusion
These five Deadline Day transfers have shown just how influential last-minute deals can be in football. They have not only reshaped the destinies of clubs but also provided an excitement and an adrenaline rush to the fans in the dying hours of the window. As each new Deadline Day unfolds, fans will always look back on these historic moves as benchmarks.
Written by: Thillai Ritvik
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