Coventry City U18's were beaten 3-2 by Crewe Alexandra.
City led through a 12th minute Blaine Rowe penalty but conceded a goal on the stroke of half-time and then in the 52nd minute.
City levelled through Lewis White in the 79th minute before Jack Burroughs was sent off for a second bookable.
In the second minute of stoppage time, Crewe broke and scored to take a win which would not have happened had City put their chances away.