It was the foreign excursion which saw the Praca de Santiago square enter Super Bock-supping supporter folklore.
And today marks 10 years since an impromptu gathering in Portugal became regarded as one of Pompey’s great away days.
It was a UEFA Cup second-leg clash against Guimaraes which ensured the Fratton faithful ventured further into Europe for their footballing fix.
Following a 2-0 home victory two weeks earlier, courtesy of Lassana Diarra and Jermain Defoe’s goals, Harry Redknapp’s side travelled for the decisive fixture.
On October 2, 2008, the Blues headed to the Estádio D. Afonso Henriques for a match which would eventually conclude the following day.
Yet before that late footballing drama, the Praca de Santiago square produced an afternoon to leave an indelible mark upon Pompey fans’ memories.
It began with handfuls of Blues followers congregating within the area for pre-match Super Bock consumption in the long build-up to kick-off.
Steadily numbers grew, with the occasional football tossed into proceedings, playfully booted in the air by ever-merry supporters for a large-scale session of keepy-uppy.
With Guimaraes police happy to stand aside and survey the action without feeling the need to sternfully intervene, spirits were high. Soon locals also joined in.
What unfolded was opposition fans drinking together, lofting a football skywards whenever possible and joining in with song under the searing Portuguese sunshine.
A number of establishments and houses around the square even allowed Blues supporters to enter and hang up flags on balconies overlooking the amicable scenes below.
Among those present in the square that afternoon were former Pompey favourites Guy Whittingham and Alan McLoughlin who, like fans, revelled in the atmosphere.
When the match finally got underway, there were tales of inebriated Pompey followers falling asleep in the away end as extra-time dragged the fixture into the next day.
Guimaraes netted twice in the opening 32 minutes to wipe out Pompey’s first-leg advantage during a rampant opening.
That sent the game into extra-time, with Peter Crouch scoring twice to hand the visitors a 4-2 aggregate success and usher them into the group stages.
Now, 10 years on, many memories of that match are a little hazy – but what occurred in the Praca de Santiago shall never be forgotten.