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Thomas Tuchel's flawless beginning as England manager was brought to a halt following a crushing 3-1 loss to Senegal at Nottingham City Ground.
This historic result saw Senegal become the first African nation ever to defeat England in men's football.
Although England struck first through Harry Kane in the opening stages, Senegal mounted an impressive comeback with strikes from Ismaila Sarr, Habib Diarra, and Cheikh Sabaly, marking England's maiden defeat against African opposition.
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The match began with Senegal creating the initial threat when Nicolas Jackson tested Dean Henderson after just five minutes, but England's goalkeeper responded with an excellent stop.
England quickly turned the tables two minutes later as Kane pounced on the rebound after Edouard Mendy could only parry Anthony Gordon's effort.
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Gordon squandered a golden opportunity to extend England's advantage near the half-hour mark, firing wide from close quarters.
This missed chance proved costly as Sarr restored parity, slotting home into the bottom corner after latching onto Jackson's cross, with the Chelsea forward catching Kyle Walker off guard.
Walker's struggles continued into the second period when El Malick Diouf exploited his positioning, delivering a superb cross that Diarra headed narrowly over the crossbar.
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Diarra wouldn't be denied for long, however, finding the net on 62 minutes by converting Kalidou Koulibaly's long pass from a difficult angle.
England's response was swift but unsuccessful, as Mendy produced two outstanding saves to thwart both Morgan Gibbs-White and Bukayo Saka.
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The hosts thought they had salvaged a point when substitute Jude Bellingham found the net with six minutes remaining, only for VAR to rule it out due to Levi Colwill's handball earlier in the sequence.
Sabaly sealed Senegal's memorable victory in stoppage time, converting from a swift counter-attack to cap off a disappointing night for the Three Lions and cement this landmark result in football history.