Town's reserves were beaten 4-3 by ten-man Portsmouth at Havant and Waterlooville's Westleigh Park on Wednesday night. The Blues' goals came from Liam Craig, a Billy Clarke penalty and Jaime Peters.
James Keene put the Hampshire side in front, but only a minute later Billy Clarke's cross was side-footed into the net by Liam Craig.
Town felt they should have had a penalty when Clarke was upended by keeper Andrea Guatelli but were denied by the referee.
However, on the half hour, the official's finger was pointing at the spot after Gregory Vignal handled a Jaime Peters shot on the goal-line, the former Liverpool man also receiving a red card. Clarke netted from the spot.
Frank Songo'o got Pompey back on terms, then Aliou Cisse put Harry Redknapp's side in front as Town missed a host of chances.
Jaime Peters equalised for the Blues but Aliou Cisse's second of the match gave the home side the points.
Late on Brian Priske cleared a Sammy Moore effort off the line as Town went looking for a fourth.
An end to end fixture which pitched the young Town reserves against a Portsmouth team including a number of experienced Premiership players. The Blues could have taken the three points had they been more clinical, Billy Clarke, who suffered what appeared to be a bad wrist injury, Liam Craig, Jaime Peters and Liam Trotter all missing decent opportunities.