Out-of-favour Tottenham striker Richarlison scored for the club’s Under-21s in an EFL Trophy penalty shoot-out at Cheltenham Town.
The 29-year-old Brazilian has seen off the likes of Everton and Vasco da Gama this summer and was not included in Spurs’ 25-man Premier League squad.
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His only senior game for the club this season came in a 3-0 defeat at Brentford on the opening weekend of the Premier League in August.
Richarlison equalized with a neat first-time finish from the right wing after George Miller had put the League Two side ahead.
Prodigy Adewole then put the young Spurs side ahead, only for Miller to score deep into stoppage time to send the tie to penalties.
Richarlison hit his shot but the home side eventually won 7-6.
Chelsea were the only winners on a difficult night for the young sides
Elsewhere, Notts County beat city rivals Nottingham Forest’s Under-21s 5-1 to book their place in the second round.
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Goals from Luke Smyth, Jacob Bedeau, Lee Ndlovu, Connor Grant and Callum Roberts put the League One side 5-0 up before Bubbacar Sanneh netted a consolation for the visitors in added time.
Oldham also finished after coming from behind to beat Leeds Under-21s 4-2 at Boundary Park.
Noah Chilvers made it 1-1 at half-time before 18-year-old Callum Mills scored his fourth goal in two games.
Carrick Njinko put the young whites in front but goals from Kane Drummond, Josh Hawkes and Kai Payne saw the home side claim victory.
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Gillingham raced into a 4-0 lead against Brighton’s under-21s before holding on for a 4-3 win.
Goals from Tom Eaves, Bradley Dack, Ethan Coleman and Louie Dayal saw the Gills cruise to a big win.
However, Shane Nti scored a brace for the visitors and Tyler Silsby added a third in the final minute.
Fulham’s under-21s also fell one goal short of a stunning comeback against their League Two rivals as they lost 3-2 at Walsall.
A Tai Sodje double and a James Furlong goal put the Saddlers 3-0 up at the break, but Jonah Kusi-Asare and Dan Casey pulled the visitors back after the break.
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Chelsea Under-21s beat League One Reading 2-0 with a first-half brace from Chizaram Ezenwata.
The Blues have five points from three games and will progress unless the Royals beat Bristol Rovers by four goals in their remaining group game.