England suffered their first defeat under Thomas Tuchel as they were beaten 3-1 by Senegal at City Ground.
The Lions of Teranga came from behind to inflict what was also the Three Lions’ first ever loss against an African opponent.
England were seeking a response from their disappointing display against Andorra on Saturday and drew first blood after just seven minutes.
Eberechi Eze stole possession and combined with Conor Gallagher to tee up Anthony Gordon, whose first-time shot was parried by Edouard Mendy for Harry Kane to tuck away the rebound.
Senegal responded well and drew themselves level five minutes before the break as Nicolas Jackson latched onto a ball over the top of the defence, before crossing for Ismaila Sarr to finish.
The visitors, who were unbeaten in 23 matches, then completed the turnaround in the 62nd minute with the Three Lions caught out by another lofted ball in behind the back line, and Habib Diarra capitalising on the space to beat Dean Henderson from a tight angle.
England thought they had equalised in the 84th minute when Jude Bellingham fired home from close range, only for the referee to rule Levi Colwill had handled in the build-up.
The hosts’ misery was compounded in the third minute of stoppage time when Lamine Camara dispossessed Curtis Jones and launched a quickfire counter, before finding Cheikh Sabaly, who controlled and tucked away.