The Owls Under-21s were dealt a cruel blow in their Under-21 Premier League Cup clash with Hull City, conceding in the final minute to slip to a 3-2 defeat.
Wednesday were off to a slow start at Hillsborough and found themselves 2-0 down inside the first ten minutes.
Greg Luer and Greg Olley struck for the visitors to stun Wednesday, who had a mountain to climb early in the contest.
But the Owls fought back and Ryan Meadows thought he had halved the deficit just past the half hour mark, when his strike hit the underside of the bar and bounced back into play.
But two minutes before the break, George Hirst latched onto a fine feed from Kyle Bailey and drilled a fierce left-footed drive into the net.
Then on the stroke of halt time, the Owls drew level.
Bailey was again at the heart of the move bursting forward after winning possession and slotted through for Meadows, who was subsequently brought down in the box.
The midfielder stepped up to convert the spot kick to send the sides in at the break level.
From that point, Wednesday assumed control of the game and a Luke Booker centre presented a good chance for Hirst to glance into the net but the cross had a fraction too much pace for the striker.
Hull’s Ben Clappison then hit the post from an angled drive before second half substitute Jack Stobbs went close with a header from a Matt Penney cross.
The ball was in the back of Cameron Dawson’s net 15 minutes from time as Jarrod Bowen slid in from close range but the strike was ruled out for offside.
Stobbs almost put the Owls ahead for the first time in the game with a curled effort towards the far post but Tigers goalkeeper Rory Watson made a good stop to keep the score level.
Hull then went a step closer as Luer saw his glancing header come crashing back off the post before the visitors ultimately grabbed the winner in the last minute.
Matthew Dixon took aim from 20 yards with a first time hit that flew into the top corner to seal the Tigers’ victory at Hillsborough.