Town's U21s fell to a disappointing 1-0 defeat against Coventry City at a bitterly cold Portman Road on Monday evening. George Thomas won the game for the Sky Blues during the second half.
Dean Gerken started in goal for his first appearance after being knocked unconscious in the early stages of the 4-1 defeat at Middlesbrough, and Elliott Hewitt featured at right-back following his recall from a loan spell at Colchester.
Town also included two trialists from the start, 17-year-old Canadian striker Dario Zanatta, who has played in the last two U21 games, and former Waterford United left-back Kevin O’Connor.
The 19-year-old Irish U16, U17 and U18 international, who can also play at left midfield, broke into the Waterford side during the 2013 Irish season, playing alongside former Blue Jack Doherty, and went on to make 44 League of Ireland appearances before leaving at the end of the 2014 season.
O’Connor, who is 6ft 2in tall, recently spent time on trial with Premier League Hull City and was offered terms before talks broke down. The Enniscorthy-born player subsequently joined AFC Bournemouth on trial.
After a fairly even opening, trialist Zanatta blazed high and wide from the edge of the box before the visitors broke and Blair Turgott rolled the ball just wide of Dean Gerken's far post.
Coventry left-back Ryan Haynes, who impressed throughout, should have given his side the lead midway through the first half but he headed wide from Maddison's cross from six yards out.
Gerken then did well to prevent Maddison's deflected effort looping over him, while Kyle Hammond pulled his effort well wide at the other end after Town's best build up play of the half.
Shortly before the interval, the dangerous Maddison struck a low left-foot shot that cannoned off the foot of Gerken's post.
Ten minutes after the restart, Thomas did give his side a deserved lead with a simple finish from close range after a fine left-wing cross from Haynes, although Hewitt will have been disappointed he didn't prevent the cross from entering the danger area.
Town responded well and Darren McQueen's crisp low drive was blocked by keeper Reice Charles-Cook, who also smothered Hammond's follow up.
McQueen then pulled a shot inches wide of Charles-Cook’s far post from a tight angle, and with 10 minutes remaining Matt Clarke headed Hammond's cross just over the bar.
Overall, the visitors controlled the majority of the play and looked comfortable in most areas, playing some nice passing football in the process.
Zanatta failed to make much of an impression during his time on the field, while O'Connor was easily beaten on a couple of occasions in the first half but looked more comfortable during the second period.
Dylan Connolly again looked dangerous and willing to run at his opponents, while Alex Henshall was unable to cause the visitors' defence many problems in front of watching first-team boss Mick McCarthy.
U21s: Gerken, Hewitt, O'Connor, Guldbrandsen (Blanchfield 74), Fowler, Clarke, Hammond, Benyu, Zanatta (McQueen 46), Connolly (Ramadan 74), Henshall. Unused: Crowe, Robinson.