The Owls Under-21s lost out by the odd goal in three against local rivals Sheffield United at Hillsborough on Friday.
Jahmal Smith struck first for the visitors from S2 after 14 minutes before Wednesday striker Andelko Savic equalised midway through the first half.
As the game seemed destined to finish honours even, United striker Jake Eyre blasted home into the top corner two minutes from time to claim victory at the last.
Wednesday started the game brightly as Adam Harvey saw his early strike well saved by Blades keeper George Willis.
A defensive lapse on 14 minutes proved costly as Smith latched onto an under-hit back pass to slot past Cameron Dawson.
But Wednesday were swiftly back in the game when Rhys McCabe’s centre was met by Savic, who diverted the ball into the far corner at the near post, out of the reach of Willis.
The Owls went close after the break when Cormac Burke played a neat one-two with Paul Corry before his strike from inside the area was smothered by Willis.
With time ticking down at Hillsborough, there was a late sting in the tail for Wednesday as Eyre’s half volley flew into the top corner to give the Blades a late advantage.
Wednesday rallied in added time and twice came close to bagging a late leveller.
First, McCabe’s half volley from 18 yards was pushed wide of Willis’ right hand up right before Johnny Fenwick’s even later header was cleared off the line by United defender MJ Kedman.