And in his time at the Fratton helm, Danny Cowley has turned to a large number of players on the pitch.
In fact, there’s been 41 men used by the Blues boss since he succeeded Kenny Jackett.
Of those 33 have played five or more times, giving a reasonable basis to assess their performances with the star and crescent on their chests.
So after that landmark 50th game with Pompey sweeping past relegation-threatened Doncaster, we’ve searched through our ratings database to see who’s performed best – and worst – under the former Lincoln boss as well as looking at who’s played the most.
Here’s what we’ve found.
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21. Louis Thompson - 6.8
Despite a difficult start at Pompey due to injuries, the central midfielder has come to life over recent weeks showing his Championship quality when fit. The 27-year-old has featured 24 times for the Blues this season and continues to play a pivotal role in Cowley's midfield in Shaun Williams and Joe Morrell’s absence. Photo: Simon Davies
22. Jack Whatmough - 6.9
The Pompey academy graduate only managed to play eight times under Cowley last season before his summer exit. After failing to agree a new deal, the 25-year-old joined Wigan where he has since played 29 times in League One as Leam Richardson's side secure Championship football. Photo: Mike Hewitt
23. Mahlon Romeo - 6.9
The Millwall loanee has been a solid figure down Pompey’s right flank, possessing defensive and attacking qualities. The 26-year-old has been vital for the Blues and has played 32 times for under Cowley this season, 29 of which were rated. Photo: Daniel Chesterton
24. Tom Naylor - 6.9
The former Blues captain played all 12 of Pompey’s games, along with MacGillivray, under Cowley before the end for the season. He was another player who failed to agree a fresh deal and joined Jack Whatmough at Wigan and has played 31 times for the Latics this term. Photo: Jason Brown