A stoppage time goal saw Town's U21 side fall to a 2-1 defeat at home to Hull City on Monday evening. Larsen Touré put the Blues ahead in the first half but a penalty from Greg Luer and Jarrod Bowen's late strike, either side of Josh Yorwerth's red card, gave the visitors the win.
Touré, Jonny Parr, Piotr Malarczyk and recently signed striker James Alabi all started for Town, alongside first-year scholar Andre Dozzell who spent last week with the England U17s.
The first chance of the game fell to Parr following Myles Kenlock's low cross from the left, but the Norwegian's effort was blocked.
Yorwerth did well to dispossess Luer on the edge of the box after some good build-up play involving Johan Ter Horst, shortly before Touré opened the scoring on the half hour.
Kundai Benyu provided a fine corner from the left side and Touré powered an unchallenged header past keeper Rory Watson from six yards out.
The Guinean international nearly turned provider seven minutes later when his curling cross came within inches of finding Shane McLoughlin, but the Irish U18 international couldn't quite stretch far enough to make contact with the ball.
The impressive Alabi caused the visitors defence further problems moments before the interval when a typically bustling run led to the ball finding Benyu on the right. His dangerous cross was diverted over the bar by Will Aimson, and Benyu's corner was then headed inches wide by Yorwerth.
Hull started the second period well and Conor Townsend stung Michael Crowe's palms with a fierce freekick struck from the edge of the Town box.
Matthew Dixon curled an effort narrowly over Crowe's bar as the hour mark approached, while at the other end Alabi nearly capitalised on a defensive lapse but his looping effort dropped wide of Watson's post.
The Yorkshire side got back on level terms with six minutes remaining. Sub Ben Hinchcliffe's cross was met by Bowen at the back post and his goalbound shot was instinctively blocked by the arm of Yorwerth, who was subsequently dismissed. Luer sent Crowe the wrong way with a good penalty into the bottom left-hand corner.
Despite Mark Kennedy reinforcing his depleted backline, the visitors scored a winner in stoppage time when Ter Horst's cross from the left was exquisitely volleyed home by Bowen from 12 yards.
A draw would probably have been a fair result with the Blues on top during the first half, and Hull having the better of the second period.
Kenlock impressed at left-back and until his red card Yorwerth had been having a solid game at centre-half alongside the comfortable Malarczyk.
Parr will have been pleased to get 90 minutes in, while Alabi's strength and desire up front will surely have impressed the watching Mick McCarthy and Terry Connor.
U21s: Crowe, Parr, Kenlock, Dozzell, Malarczyk, Yorwerth, Toure (Ford 77), Benyu, Alabi, McLoughlin (Ramadan 55 (Robinson 86)), Henshall. Unused: Wright, Maynard.
Hull: Watson, Clackstone, Townsend, Dixon, Aimson, Clappison, Annan (Hinchcliffe 58), Clark, Luer, Ter Horst, Bowen. Unused: Saltmer, Olley, Rodgers, Barkworth.