Izale McLeod had warned there are days like this, certainly the voice of experience in the build-up to the match.
A year earlier he was part of a struggling Barnet side which triumphed at Fratton Park in the Carling Cup.
Fast forward to the present and he could appreciate life on the other side of the fence.
Of course, not a single Pompey player remains from that abject 1-0 defeat on that August 2011 evening.
Long since departed, the vast, vast majority of them embarked for Championship destinations during the summer.
This time around, there was a completely new team containing McLeod, a different manager in Michael Appleton and an alternative competition in the form of the Johnstone’s Paint Trophy.
Akos Buzsaky was even granted his much-anticipated full debut in an attacking central-midfield role.
Yet last night’s outcome was precisely the same, with lowly League Two Wycombe leaving Fratton with a victory.
Humiliating, embarrassing, sloppy – there were unquestionably no positives to be taken from the performance of an almost full-strength Pompey team.
The damage was essentially wreaked in the opening 17 minutes. Certainly the Blues never recovered from such a wretched start.
Joel Grant curled home a sublime finish after a mere 13 seconds and so began a torrid spell which would see Jo Kuffour hit the left-hand post twice.
Throw in Dean Morgan’s scrambled effort to increase the Chairboys’ advantage and Pompey were reeling with barely a third of the first half gone.
McLeod’s close-range finish, his fifth goal in eight games, did, at least, reduce the deficit in first-half stoppage time.
However, Adam Webster tripped debutant Bruno Andrade in the 56th minute and Morgan scored at the second attempt following Simon Eastwood’s initial save from his penalty.
Pompey huffed and puffed afterwards but failed to create sufficient goalscoring opportunities to reduce the scoreline.
In truth, nor did they deserve to on a damp and depressing night on the south coast.
Instead, it was Wycombe, a side lying one place above the trap door to non-league football, who march into the next round of the Johnstone’s Paint Trophy.
Before the match, Buzsaky was, as expected, granted his full Pompey debut, but Appleton also made a surprise by barely changing any of his other personnel.
There were just two different faces in the starting line-up compared to the team which secured a point at MK Dons at the weekend.
With Mustapha Dumbuya on international duty with Sierra Leone, Buzsaky came into the side, prompting a reshuffle.
Webster shifted to right-back, with Jon Harley dropped into his more accustomed left-back role.
In turn, Buzsaky was given a central-midfield spot at the point of a diamond system, with Brian Howard sitting deep.
The only other change was Eastwood selected in goal in place of Mikkel Andersen.
It represented the former Huddersfield stopper’s Fratton Park debut – and it got off to a disastrous start.
Wycombe took the kick-off, and within 13 seconds they had taken the lead before a Pompey player had even managed to touch the ball.
It was Grant who did the damage, picking up possession outside the box and curling a magnificent right-foot shot into the far corner of the net.
Just seven minutes later the hosts received a let-off when Kuffour cut into the area, leaving Lubomir Michalik flat-footed, and drove a shot against the left-hand post.
But in the ninth minute Wycombe did double their advantage.
Eastwood had already pulled off two stops during an almighty scramble in the six-yard box but, in the end, Morgan was on hand to squeeze the ball home from close range.
McLeod would be the first to test the Chairboys keeper when, on 11 minutes, he fired in a shot which Nikki Bull saved low down.
Moments later, a Howard corner from the left was met with a powerful Gabor Gyepes header which was brilliantly tipped over the bar from close range.
Midfielder Johnny Ertl was the next to fire in an attempt on goal, drilling in a shot from the right which was comfortably gathered by Bull.
However, it was Wycombe who then again came closest to scoring, with Kuffour once more unfortunate with 17th minutes on the clock.
Dave Winfield cut out a pass intended for McLeod and the ball fell to the Wycombe striker who surged into the box before curling a shot against the left-hand post.
At the other end, a patient build-up involving Lee Williamson and Buzsaky saw Wes Thomas being fed the ball, and he produced a clever turn before firing over the bar.
The match was wide open and Pompey had appeals for a penalty waved away on the half-hour mark when the on-loan Thomas was sent tumbling in the area under a challenge from Matt Spring.
Buzsaky made his intentions known in the 37th minute with a thunderous shot from 30 yards which had Bull smothering it at the second attempt.
Appleton’s men did pull one back on the stroke of half-time, though, when Bull was unable to hold on to Thomas’ cross-shot.
McLeod was on hand to ram the ball into the roof of the net from close range to give the home side a timely lifeline and Blues supporters hope of a comeback.
Within 11 minutes after the interval, however, Wycombe regained their two-goal advantage after Webster had fouled Andrade inside the penalty area.
Morgan’s spot-kick was magnificently saved by Eastwood diving to his right but the striker managed to head the rebound into the net.
Pompey responded by bringing on Ashley Harris and, moments later, Bull clawed away another Gyepes header, this time from a Buzsaky corner.
The Fratton faithful chimed in with a rendition of ‘Always Look On The Bright Side Of Life’ as the match reached its inevitable conclusion.
After all, last night was an experience they have tasted before – just over a year ago.