Two goals in the final two minutes saw the Blues’ U21s fall to a 3-2 defeat to Charlton at Portman Road, Jay Emmanuel-Thomas and Jack Marriott netting for Town.
The Addicks had the best chance of the opening 20 minutes with captain Bradley Jordan putting the ball past the right post from inside the box.
Town took the lead in the 28th minute with the ball coming to Emmanuel-Thomas in the box, who took a great first touch to create some space and then swivelled and shot, sending the ball into the bottom left corner.
Four minutes later and the visitors were level. Town, unable to clear their lines from a corner, allowed Harry Lennon to score from virtually the goalline with it looking as though Lee-Barrett may have done better.
The Addicks started the second half strongly and Joe Pigott came close to scoring with a good shot from the edge of the area forcing Arran Lee-Barrett into a good save, low to his left. Pigott had another opportunity minutes later with the striker scuffing his shot at the back post.
Town had one of their few chances of the game when Tyrone Mings played the ball to Byron Lawrence in the box, who saw his shot blocked.
Lawrence had another chance in the 56th minute with a volley from outside of the area that went just wide of the left post.
The visitors came within inches of scoring just after the hour mark. Skipper Jordan ran to the each of the area and struck a shot which was deflected onto the bar.
Town had a couple of half chances approaching the last 10 minutes with Emmanuel-Thomas heading wide from a corner and then having a shot blocked inside the box.
The Blues scored what looked to be the winner with four minutes remaining when Elliott Hewitt's cross was deflected to Marriott in the box. The striker turned and fired the ball across the keeper into the bottom left corner.
Two minutes later and with two minutes remaining the score was level. A cross to the back post found unmarked Pigott who headed in.
The visitors got a 90th minute winner with Pigott again on target. This time he latched on to a through ball before slotting his shot into the left corner of the goal.
In front of the watching Mick McCarthy, Anthony Wordsworth played the full game on his comeback from injury and looked bright in the middle of the park with some good deliveries from freekicks.
Trialist Thomas Gardiner, an 18-year-old defender from Tottenham, put in a quiet display in a not overly inspiring U21s performance in which few individuals stood out.
U21s: Lee-Barrett: Hewitt, Mings, Clarke (Berkane 51), Kisnorbo, Gardiner, Emannuel-Thomas, Wordsworth, Marriott, Lawrence (C), Timlin (Galvin 70).
Charlton: Button, Osborne, Fox, Feeley, Lennon (Powell 45), Cousins, Gower, Hollins, Jordan (C), Azeez, Pigott.
Report: Blair Ferguson