Now Michael Doyle and Kyle Bennett have reunited – at the club where the Blues sealed their promotion.
Doyle has spent the last two-and-a-half years at Notts County, culminating in last month’s appointment as player-assistant head coach.
And it appears he is already having an influence in the Magpies’ recruitment following the arrival of Bennett.
His ex-Pompey team-mate has suffered a difficult time since leaving Fratton Park in January 2018 under Kenny Jackett.
After initially impressing at Bristol Rovers, the winger then fell out of favour over the next three-and-a-half years.
He spent the majority of last term on loan at League Two Grimsby, making just 15 appearances and unable to prevent their relegation out of the Football League.
Now, following his Rovers release, the 30-year-old has arrived at Meadow Lane as a triallist seeking a new home.
Bennett marked his first game for the National League club with an impressive display in Saturday's 2-0 friendly win over Coalville.
Firstly, his fierce shot against the post was converted by ex-Pompey loanee Damien McCrory for the opener.
Then Bennett sealed the success with a superb 20-yard effort, which left Magpies boss Ian Burchnall purring.
Burchnall told Nottinghamshire Live: ‘You can see obviously that he's been at a good level and he's got lots of quality.
‘He was great with the ball and dropped down to make things happen.
‘He came on in the second half. The boys in the first half did a great job to kind of take the brunt of the tempo, and then our lads could control it a bit more in the second.’
Bennett arrived at Fratton Park in the summer of 2015 as Paul Cook’s first signing – and went on to make 117 appearances, scoring 13 goals.
He netted in five of the last 11 matches as the Blues claimed the League Two title in 2016-17, that tally including registering in the 6-1 crushing of Cheltenham on the final day.
Bennett went on to make 62 outings for Bristol Rovers, scoring four times, before released this summer.
A message from the Editor, Mark Waldron
The News has launched a subscription offer which gives you unlimited access to all of our Pompey coverage, starting at less than 14p a day.
You can subscribe here to get the latest news from Fratton Park - and to support our local team of expert Pompey writers.