A goal from trialist striker Leon Best wasn't enough as Town's U23 side fell to a 3-2 defeat to Birmingham City at Playford Road on Monday afternoon.
Free agent former Ireland international Best started in the centre of a front three, with Luke Varney on the left and youngster Shane McLoughlin on the right.
Tommy Smith and Paul Digby started at centre-back with Andre Dozzell ahead of them in a central midfield role.
The Blues began the game well and came close to netting inside the first couple of minutes. Dozzell's effort was blocked but the rebound was then deflected towards goal by Best, who saw the ball gathered on the line by Jake Weaver. The keeper wasn't to know that an assistant had flagged Best offside seconds earlier.
However, with their first attack of the game in only the fourth minute the visitors took the lead. Viv Solomon-Otabor's straight cross from the left was met by the on-rushing Wes McDonald and he side-footed the ball into the net from six yards out.
Birmingham left Town shell-shocked as they doubled their advantage within a minute. A simple ball over the top of Town's backline, who appealed in vain for offside, was lobbed over the advancing Michael Crowe by Kyle McFarlane.
Dozzell's freekick was clawed away from the top corner by Weaver soon after, before Town pulled a deserved goal back on 13.
Trialist Best collected the ball on the halfway line and showed great strength and pace to get away from Luke Maxwell, before producing an impressive low finish across Weaver and into the far corner.
Varney headed Josh Emmanuel's cross from the right just wide, but Birmingham were clinical at the other end and they scored a third shortly after the half-hour mark.
McLoughlin was dispossessed in a dangerous area and Reece Brown's neat flick released McFarlane, who slid the ball under Crowe.
Two minutes before the interval Town were awarded a penalty. Referee Elliott Kaye ruled that a Town shirt had been pulled in the box following a corner from the right. Dozzell stepped up to take the spotkick but saw his low effort pushed away from the bottom corner by Weaver.
McFarlane twice came close to extending the visitors' lead in the opening 10 minutes of the second half, before Ben Morris replaced Best on the hour mark.
It looked to be a pre-planned substitution but the former Rotherham striker will have impressed the watching Mick McCarthy and Terry Connor with a combative and lively display, particularly during the first 45.
Moments after Morris's introduction, Adam McDonnell reduced the arrears with a right-foot shot from the edge of the box which Weaver and one of his defenders failed to prevent crossing the line.
Midway through the half Morris produced a good run and released Varney, but his powerful attempt was well kept out by Weaver.
Morris then had Town's best chance to get back level when he met Emmanuel's cross from the right, but the England U17 international could only direct his header back across goal and wide of the target.
The final action of the match saw Crowe produce a fantastic one-handed stop to keep McFarlane's effort from six yards out. The dangerous striker had turned in the box and struck a powerful volley which looked destined to hit the net before Town's keeper somehow blocked it.
Overall it was an entertaining game and a draw would probably have been a fair result.
Best will be hoping to be offered some sort of deal by Blues boss McCarthy, while Smith impressed with an assured and confident display on the left side of the central defensive pairing.
Town: Crowe, Emmanuel, Kenlock, Blanchfield, Digby, T Smith, Varney, McDonnell, Best (Morris 60), Dozzell, McLoughlin (Patterson 41). Unused: Robinson, Marsden, C Smith.