Adam May represents Pompey’s sole representative in the FA Cup following Sutton United’s dramatic progress.
And it was two former Blues players who inflicted Saturday’s surprise 2-1 defeat on Cheltenham Town.
Danny Wright had put the League Two visitors ahead in the 34th minute, yet a second-half fightback left them stunned.
The familiar face of Matt Tubbs marked his debut for the National League side by levelling on 46 minutes.
The experienced striker was snapped up by Paul Doswell earlier in the week following a frustrating time at high-flying Forest Green Rovers.
The former Pompey forward was replaced in stoppage-time by May, who is currently on loan at Gander Green Lane.
Then, moments later, Roarie Deacon netted a memorable winner, five minutes time added on.
Deacon spent a week on trial at Fratton Park and then Cambridge United in the summer during a search for a club following his Crawley release.
It was Doswell who snapped him up, with the winger going on to score against Pompey in Sutton’s 2-1 pre-season victory.
Deacon has netted seven times and weighed in with 11 assists this season – a haul prompting him to be linked with Bristol Rovers and Charlton.
Now the U’s await the outcome of tonight’s third-round draw, with Premier League clubs entering for the first time.
With May’s loan scheduled to expire in January, it remains to be confirmed whether the length of his stay includes the FA Cup.
Nonetheless, following Pompey’s elimination by Wycombe at the first-round stage, the midfielder at least adds interest for Blues followers.
Meanwhile, Tubbs will be hoping for regular first-team football under Doswell.
Following his release by mutual consent from Pompey in the summer, he linked-up with the ambitious Forest Green.
He scored twice in 12 appearances before last week being allowed to depart the third-placed team.
There was also a loan spell at Woking, with three goals in six outings.
Tubbs scored 14 goals in 40 matches for Pompey after arriving in January 2015 from Bournemouth.
Following injury, he fell out of favour with Paul Cook in the second half of last season and was loaned out to Eastleigh.