Gareth Evans reminisced on it ahead of his 200th Pompey appearance at AFC Wimbledon.
‘I was thinking about it the other day, I don’t think there's been a triallist that has signed since me,’ said the fans’ favourite.
Indeed, Evans was correct in his assessment. He was the last free agent to win himself a Fratton Park deal.
Of course, plenty have tried since – both under Paul Cook and since Kenny Jackett succeeded him as manager.
But while Cook handed contracts to Evans and Ben Davies, Jackett's yet to reward a triallist with a permanent stay.
In truth, most unattached players the boss has run the rule over were never going to be rewarded with terms.
Paul Paton is now in the Scottish second tier outfit Dunfermline, while Aaron Jarvis has scored only three times in 15 matches for Sutton after training with Pompey in the summer.
They’re just three names who can be rattled off. The list goes on.
Ceykan Karagozlu is likely met with a furrowed brow – and there are plenty more akin to him.
Let's face it, not many former triallists have gone on to make Jackett regret his decision – except maybe one.
Bruno Andrade will line up for Lincoln when they travel to Fratton Park tomorrow night.
The Portuguese is a name that will be familiar with fans as he was once on the Blues’ radar.
He wasn't a free agent when he turned up at the Blues' Roko training base in October 2017, however.
Having dropped down to non-league football after departing QPR, he was the sort of player that fitted in to Jackett and the Eisner’s recruitment policy – someone hungry for another chance in the Football League and still young enough to improve and be sold for a profit.
With Andrade under contract at Boreham Wood, it meant the Blues would have had to pay a fee and wait until January for him to become their player, if they had made a move.
Ultimately, Jackett decided against lodging a bid, with the wide man remaining at the Wood for the remainder of the campaign, which culminated in play-off final defeat to Tranmere.
Andrade was to make a Football League return after his Boreham Wood contract expired, though, completing a switch to Lincoln after they won the National League title.
There he’d continue his hurtling progress under the Cowley brothers.
He was a regular starter, plundering 11 goals and eight assists in 50 appearances as the Imps claimed the League Two title by six points last term.
Such exploits resulted in Pompey once again being linked with a switch for Andrade over the summer, although Jackett instead opted to sign Marcus Harness and Ryan Williams to bolster his wide options along with Ronan Curtis.
This campaign, Andrade has found it tougher as Lincoln acclimatise to their new third-tier surroundings, now under former Blues boss Michael Appleton.
The-ex Woking ace has remained a key player, though, scoring two and creating two in 18 games, with one of his goals an outstanding volley in a 4-2 Carabao Cup loss to Everton.
Jackett will undoubtedly be happy with the wingers he has as Pompey now aim to remedy their faltering start to the campaign.
But when Lincoln arrive on the south coast, Andrade will have designs on coming back and haunt the side that were once potential suitors.