Pompey marked their 31-year return to the Hampshire Senior Cup with a defeat at Andover New Street.
A Blues side made up of Mark Kelly’s academy troops fell to a 2-1 second-round loss at the Wessex League premier division basement side.
Alfie Stanley had given the visitors a second-minute lead but goals either side of half-time from Shane Lock and Callum Sweeney dumped Pompey out of the county competition.
The game started at a frenetic pace and the hosts should have taken the lead within the first minute.
Lock’s cross from the left was met by Zac Neve and he headed narrowly wide.
Pompey punished that error by going up the other end and taking the lead just a minute later.
Josh Flint’s cross picked out Stanley in the area. His first shot was stopped by home keeper George Paxter before the striker found the back of the net at the second attempt.
Stanley could have doubled his tally on five minutes but scuffed Harry Kavanagh’s cross from the right.
From there it was Andover who had the better of the play.
First Lock headed wide from a deep free-kick in the 12th minute before Pompey keeper Leon Pitman swallowed up Sweeney’s long-range shot eight minutes later.
Stanley was the Blues’ main attacking outlet and his 22nd-minute shot from close range was thwarted by Baxter.
The Wessex League outfit continued to push for an equaliser and got their reward six minutes before the break.
A goalmouth scramble ensued from Sweeney’s corner and Lock hooked the loose ball home.
On the stroke of half-time, Andover almost took the lead but Pitman produced a decent stop from Luke Weller’s close-range free-kick.
Pompey started the second half brightly, with Stanley having a one-on-one effort saved by Baxter.
But New Street took the game by the scruff of the neck.
Pitman produced a superb diving save to keep out Weller’s angled left-foot shot in the 49th minute.
On 58 minutes, Sweeney met Kieron Le Brun’s cross but headed wide.
However, it was that man Sweeney who gave the hosts a deserved lead three minutes later.
Lock picked out the Andover forward and he rifled a left-footed shot into the far corner.
Pompey did press for an equaliser and Stan Bridgman may have done better when he failed to find an empty net in the 71st minute.
In the 86th minute, Ethan Robb headed Freddie Read’s corner off target.
And then in stoppage-time, Haji Mnoga’s effort was deflected over the crossbar and Pompey’s hopes ended.