It kicked off against Dagenham & Redbridge, now Newport County will provide a notable landmark.
Saturday represents 100 Pompey matches for boss Paul Cook as he strives to perform the promotion requisite.
During a footballing era when managerial life-spans are ever-diminishing, his continued Blues presence signals something of an accomplishment.
Following his Fratton Park appointment on May 12, 2015, only 21 bosses in the top four divisions have served longer in their current jobs.
In terms of Pompey, Cook is the first since Harry Redknapp to reach three figures at the helm.
Of course, the man who masterminded the 2008 FA Cup victory had two spells with the Blues, exceeding 100 matches in both.
Following the end of this second tenure in October 2008, upon his departure for Spurs, Redknapp had racked up a total of 243 games.
Since that exit, only Steve Cotterill (61) and Andy Awford (55) have passed the half-century mark for matches, putting Cook comfortably ahead of his recent predecessors.
What’s more, the current incumbent boasts the Blues’ second-highest win ratio over the past 40 years.
For Cook, life in the Fratton hot-seat began with a 3-0 triumph over the Daggers on the opening day of the 2015-16 campaign.
Kyle Bennett netted twice and Gareth Evans grabbed the other – from a Bennett left-wing corner – as they marked their Pompey debuts with goals.
Fitness permitting, both can expect to start Cook’s 100th match in charge against struggling Newport this weekend.
The side on that sunny August day also included current first-team regulars Christian Burgess, Matt Clarke, Enda Stevens and Michael Doyle.
Gary Roberts has found himself on the bench in recent weeks, while fellow starters that day – Brian Murphy, Ben Davies, Nigel Atangana and Matt Tubbs – have since left the club.
A crowd of 16,948 were present for a glorious start to the Cook reign, as the first weekend of the campaign saw Pompey second in the table.
The former Chesterfield boss targeted promotion that season, yet his team lost out in the play-off semi-finals to Plymouth.
Regardless, the sixth-placed finish represented a leap from a club-record low of 16th the previous campaign.
This term has seen the Blues remain in touch with League Two’s automatic promotion spots and they currently occupy third, with a four-point cushion.
With eight matches remaining, including the visit of an Exiles side second from bottom, there remains a confidence Cook can lead them into League One.
When analysing managers’ records during the past 40 years, his win ratio of 45.45 per cent puts him behind Redknapp’s first spell in charge (46.55 per cent).
Cook stands ahead of Bobby Campbell (43.11), Redknapp’s second spell (42.51) and Frank Burrows’ first spell (42.40).
And with 45 victories, how Pompey need a 46th on Saturday.