He was one of the instigators the last time Pompey suffered a cup defeat at Fratton Park.
Now Izale McLeod is on the opposing side hoping to fend off similar aspirations from Wycombe Wanderers tonight.
The League Two side are currently just one spot above the trap door into non-league football after a wretched start to the campaign.
Manager Gary Waddock was replaced by caretaker Gareth Ainsworth last month, who managed to steer the Chairboys to a 2-1 victory over Torquay at the weekend.
Now they travel to the south coast for tonight’s Johnstone’s Paint Trophy second-round clash.
McLeod was part of the Barnet side which pulled off a shock 1-0 victory over Pompey in front of 4,464 supporters in August 2011.
Lawrie Sanchez’s strugglers were indebted to Mark Hughes’ 30th-minute winner for that Carling Cup first-round surprise against a strong Blues side.
The likes of Greg Halford, Ricardo Rocha, Hayden Mullins, David Norris, Joel Ward, Luke Varney, Dave Kitson, Stephen Henderson and Liam Lawrence all lined up for Steve Cotterill’s side that night.
This time around, the in-form McLeod will be striving to prevent a repeat performance. And he has warned his team-mates to underestimate the League Two strugglers at their peril.
McLeod said: ‘Wycombe is going to be a tough game. They are going to come to win and the gaffer is going to put a side out wanting to win.
‘It’s going to be another difficult one but we will go out and give it our all again
‘From experience, I know you have just got to go out there and work hard. Treat it as any normal game.
‘If we go out and underestimate Wycombe in any way or not work as hard as we have done in the past three games, then that is a potential banana skin right there.
‘But if we go out and perform to our maximum – each and every one of us – I am sure we will get a good result.
‘I remember with Barnet we went there (Fratton) with a game-plan. Everyone worked hard, raised our game and played well. We got the result.
‘Each and every individual game is different but, for a start, we have got to work hard. If we implement our game-plan well tonight and work hard as a team then I am sure us – as players – will expect to win the game.’
Michael Appleton is expected to make several changes to his side tonight.
Akos Buzsaky will definitely be in the starting line-up from the team which drew 2-2 at MK Dons at the weekend.
Jack Compton, Jordan Obita, Luke Rodgers and Liam Walker could also come into contention.
However, Josh Thompson and Darel Russell are still sidelined through injury.
McLeod himself is waiting to see whether he will get the opportunity to add to his four goals in his past seven matches.
And, if named, there is a new penalty-taker in town.
He added: ‘I have already called that job so I will be looking to take it.
‘Brian (Howard) was our penalty-taker but now he has stepped aside and I will look to take the next one.’