Sky Blues U21s have fallen to defeat at The Alan Higgs Centre, beaten 2-1 by Sheffield Wednesday.
The visitors took the lead early on Allard Way, before Harrison Nee found an equaliser with 15 minutes left on the clock.
But Max Hayforth's late strike secured the win for Wednesday, their first since the opening day of the season.
The young Sky Blues started brightly, with both Tom Costello and Marco Rus seeing goal-bound shots blocked during the early phases.
However, it was the visitors who had the best of the early chances with both Bailey Cadamarteri and Leojo Davidson hitting the side netting from close range.
Wednesday would take the lead on 13 minutes, through a well-struck effort from Cadamarteri. The youngster wriggled inside before curling his shout across Billson’s goal. The City stopper was able to get a hand on the shot, but could not prevent it from finding the net.
Wednesday’s flurry of chances continued, with Davidson twice coming close to doubling his side’s lead, but the forward was denied by an impressive Billson.
Fabio Tavares came close for Coventry, just before the half-time. The jet-heeled forward found space down in the channel, but saw his effort from wide whistle past the near post.
After the break, Dempster made changes with Will Bapaga and Harrison Nee entering the fold - and it was Nee who fired city level with 13 minutes left on the clock, turning in a Tavares shot.
Late in the game, Dempster made two further changes. Dermi Lusala and Aidan Finnegan both entered the fold as Josh Eccles and Todd Kane left the scene. However, neither were able to stop Wednesday from snatching a winner late on, when Max Haygarth fired home from the edge of the area.
Goal(s): Bailey Cadamarteri 13', Harrison Nee 77', Max Hayforth 83'.
Yellow Cards: Will Trueman 41', Adam Adetoro 66'.
Red Cards: None.
Sky Blues U21s XI: Tom Billson; Todd Kane, Abel Alabi, Jay McGrath, Josh Reid, Jack Burroughs; Ryan Howley, Josh Eccles, Marco Rus; Tom Costello, Fabio Tavares.
Subs: Luke Bell, Dermi Lusala, Aidan Finnegan, Will Bapaga, Harrison Nee.