Pompey bowed out of the FA Cup at the first hurdle after a 2-1 loss to league rivals Wycombe Wanderers at Fratton Park.
Gareth Evans fired the Blues level early in the second half after former Pompey academy graduate Paris Cowan-Hall had given the visitors a 26th-minute lead.
But despite a much-improved performance from Paul Cook’s men after the break, Adebayo Akinfenwa won it for Wycombe with six minutes to go with a looping header.
The Blues were lacklustre in the first half and it was no surprise when the visitors went ahead. Joe Jacobson whipped in a free-kick which David Forde punched away. But as the ball hit Christian Burgess, Cowan-Hall was left with a simple tap-in.
Thankfully, Pompey sparked into life in the second half and their increase in tempo was quickly rewarded when Enda Stevens’ low cross from the left was turned home by Evans.
Just as the Blues pressed for the winner, though, Wycombe booked their second-round spot on 84 minutes as Forde once again failed to deal with a cross.
The keeper raced out to punch the ball away but, as he was off his line, Akinfenwa was able to loop a header into the net.
Pompey should have levelled with the last kick of the game when Kyle Bennett’s deep corner found Stevens. But the Irishman headed over from close range as the Blues made a swift exit from this season’s competition.