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Home » Raheem Sterling left Chelsea in dramatic one-in-one-out transfer on deadline day
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Raheem Sterling left Chelsea in dramatic one-in-one-out transfer on deadline day

By staff1 September 2025No Comments5 Mins Read

Chelsea snapped up Jadon Sancho on a loan deal from Manchester United after allowing his fellow England international, Raheem Sterling, to leave the club for Arsenal

Raheem Sterling  and Jadon Sancho of England during a training session at Staplewood on September 09, 2019 in Southampton, England.
The two former England regulars were involved in a one-in-one-out deal at Chelsea(Image: Robin Jones/Getty Images)

Raheem Sterling swapped one London club for another at the last minute in 2024, allowing Manchester United’s Jadon Sancho to escape Old Trafford and head to Chelsea. Last year’s deadline day was full of surprises in the Premier League, with Chelsea’s dramatic dealings sparking plenty of headlines.

Two deals involving Chelsea, Arsenal, and United saw Sancho and Sterling move to different parts of London on loan for the new campaign. As the transfer window slammed shut, the Blues released a small statement confirming Sterling’s departure, which simply read, “Good luck, Raheem.”

The then-29-year-old winger – who is now 30 years old and back at Stamford Bridge – completed a last-minute loan switch to the Emirates Stadium. This was after it became clear he was not part of manager Enzo Maresca’s plans at the club, with Pedro Neto and Joao Felix both joining the club throughout the summer.

READ MORE: Man Utd transfer news: Red Devils set to complete striker deal as boss speaks outREAD MORE: Arsenal transfer news: Gunners agree £45m deal as four exits in the balance

Chelsea saw another new addition to their squad: the arrival of former Dortmund winger Sancho, who essentially was swapped in for Sterling. The England international was also left out of then-boss Erik ten Hag’s plans at United and had been free to depart either on loan or on a permanent deal.

Stamford Bridge was the chosen location for the young attacker, as United agreed to an obligation to buy price of £23million if certain targets were met. That was a far cry from the £73.5m that the club paid back in the summer of 2021 to lure Sancho to Manchester, but he hardly pulled up trees at Old Trafford, registering just 12 goals and six assists in 83 appearances, subsequently seeing his stock fall dramatically.

Meanwhile, Sterling was reunited with an old friend at Arsenal; boss Mikel Arteta, who spent a lot of time working under Pep Guardiola during the forward’s seven-year tenure with Manchester City.

Raheem Sterling of Arsenal reacts during the Premier League match between Arsenal FC and Crystal Palace FC at Emirates Stadium on April 23, 2025 in London, England.
Sterling reunited with an old friend at Arsenal, but wasn’t as successful as he might’ve hoped(Image: Ryan Pierse/Getty Images)

Sterling’s deal did not include an option or obligation to buy, meaning he would return to Chelsea at the end of the 2024/25 season regardless of his impact in north London.

During his time at Arsenal, the forward managed just one goal and assisted five times in 28 appearances across all competitions, including the Champions League. Sterling was used sparingly and arguably enjoyed his best game when he helped Oleksandr Zinchenko and Declan Rice score in a 2-2 draw with PSV in their last 16 clash in Europe’s elite competition, sending them through 9-3 on aggregate.

He also made some contributions in the League Cup and Premier League, but ultimately finished the season without silverware and barely any game time before heading back to Stamford Bridge.

Meanwhile, Sancho had a more impactful year with Chelsea, scoring five goals and assisting 10 times across 41 appearances both domestically and in Europe. Most of the young winger’s goals came in the Premier League, but it was in the knockout stages of the Conference League where he shone the most for the Blues.

Jadon Sancho of Chelsea poses for a photograph with the UEFA Conference League trophy after his team's victory in the UEFA Conference League Final 2025 between Real Betis Balompie and Chelsea FC at Stadion Wroclaw on May 28, 2025 in Wroclaw, Poland.
Jadon Sancho fared much better at Chelsea last season(Image: Darren Walsh/Chelsea FC via Getty Images)

After making the Champions League final with Borussia Dortmund while on loan in the 2023/24 season – which they lost 2-0 to Real Madrid – Sancho made yet another European final, this time with Chelsea.

The Blues faced Real Betis – and fellow United loanee Antony – in the final, and they dispatched the Spanish club in style, winning 4-1 with Sancho scoring the third in the 83rd minute of the game.

However, Chelsea opted not to pay a fee to United to avoid having to trigger Sancho’s buyout clause, having failed to be convinced by the winger despite his role in helping them claim silverware.

Now, Sancho is part of Ruben Amorim’s ‘bomb squad’, with the club still trying to secure a move away for the winger as he is not part of the Portuguese manager’s plans for the future.

Sancho has already turned down moves to Roma and Besiktas but is reportedly wanted by several clubs, while Sterling is also unwanted at Chelsea. With both players in difficult positions at their clubs, there’s every chance they could one again be involved in a dramatic deadline day move, and will hope this time they can make more of an impact if they do end up joining new clubs.

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