Rotherham United fell to a penalty shootout defeat to Manchester City’s Under-23s in the opening game of the Checkatrade Trophy.
The Millers looked set for victory when David Ball gave them a 64th-minute lead, calmly slotting the ball home after Alex Bray’s through ball.
But Benjamin Garre levelled four minutes into stoppage time to send the tie to a shootout.
And Rotherham quickly fell behind on spot-kicks after Will Vaulks and Jon Taylor failed to convert.
Anthony Forde and Jonson Clarke-Harris did manage to score their penalties but Charlie Oliver made it 4-2 to City to earn the two-time Premier League champions’ youth team the victory.
The Millers still take a point from the game, with City earning two.
Rotherham: O’Donnell, Cummings, Dominic Ball, Wood, Purrington, Forde, Vaulks, Taylor, David Ball (Kayode 84), Clarke-Harris, Yates (Bray 57). Unused substitutes: Bilboe, Hinds, Murr, McGinley.
Man City U23: Muric, Duhaney (Matondo 75), Oliver, Latibeaudiere, Francis, Smith, Davenport, Dele-Bashiru (Richards 70), Dilrosun, Nmecha, Gonzalez (Garre 62). Unused substitutes: Wilson, Haug.
Referee: A Backhouse (Cumbria).
Aston Villa dropped into the Sky Bet Championship relegation zone after losing 2-1 at Reading.
Steve Bruce’s men found themselves behind four minutes into the second half when Glenn Whelan deflected Adrian Popa’s cross into his own net, which goal-line technology confirmed had crept in.
The Royals, beaten on penalties in last season’s play-off final, then doubled their lead after 55 minutes through a close-range effort from Mo Barrow.
Villa, one of the pre-season promotion favourites under new skipper John Terry, pulled a late goal back through Conor Hourihane but it was not enough to prevent them slipping into the bottom two.
Ipswich also have maximum points after a late goal from Jordan Spence secured a dramatic 4-3 win at Millwall.
Bristol City grabbed an equaliser deep into eight minutes of stoppage time to bag a 2-2 draw at Brentford.
Everton have agreed a deal worth up to £45m for Swansea playmaker Gylfi Sigurdsson.
The Icelandic playmaker will undergo a medical on Wednesday to finally complete his protracted transfer to Goodison Park.
The saga has dragged on for most of the summer with Swansea initially valuing the 27-year-old at £50m.