Since being appointed permanent head coach on Monday, despite failing to guide Pompey into the League One play-offs, plans for the 2021-22 season are already full steam ahead.
The first major acts Cowley must carry out is decide on the futures of the 11 out of contract players.
Plenty has been made about the number whose deals have culminated now the campaign is over.
Included in the group are captain Tom Naylor, Jack Whatmough, Ryan Williams and Craig MacGillivray – who’ve all been regulars when fit.
With Cowley plotting a renewed League One promotion push, he has to decide who out of the 11 can make an impact next term and who is surplus to requirements.
With that said, we’ve taken a look at what the head coach has previously said about each of them since taking the hot seat from Kenny Jackett in March...
1. Tom Naylor
The skipper said in April how he wants to extend his stay at Fratton Park and that the Cowley’s have also said they want to keep him. Naylor missed just 18 minutes of action under the former Huddersfield boss’ time in the driving seat. Speaking after being unveiled as interim head coach, Cowley said: He’s a good solid, dependable human being. Really liked and has a deep care for the football club. He's combative, good at putting counter-attacks out and the group thinks a lot of him. He does an awful lot of selfless things, put the team first, you can't have enough of those.’ Photo: Joe Pepler
2. Jack Whatmough
Danny Cowley has not hidden how much that he rates the homegrown defender. Cowley’s previously lauded the Gosport-born ace as a Championship player in the making. Speaking last month, he said: ‘He’s got a really nice balance of defending first. He’s a centre-half, so they’ve got to defend. I wouldn’t want to put a ceiling on how far he can go, to be honest. I’ve seen the Championship and he’s well, well, well capable of that.’ Photo: Joe Pepler
3. Andy Cannon
The midfielder’s nursed a back injury since Cowley arrived at Fratton Park, limiting his number of minutes. However, it was the 1-0 win at Wigan when Cannon has his best game, scoring a superb 30-yarder only second after coming on at half-time. Cowley said: ‘Andy Cannon’s a top player, there’s no doubt about that. He’s a talented boy isn’t he, he’s a really talented boy. He trained on Saturday morning after the Friday game and was really good. I picked a few bits of him in training. That goal (Wigan) was a goal out of sync with the game because it was always going to be a difficult game on that pitch.’ Photo: Daniel Chesterton
4. Ryan Williams
The Aussie’s work-rate has left Cowley plenty impressed since taking the helm . Speaking after the 2-1 win at Shrewsbury, Cowley said: ‘He wants to run around and you’ve just got to get him in a position to free him up where he’s going to go and press, go and run. His penetrative runs are brilliant, he makes so many sacrificial runs where he’ll make a run and knows he won’t get the ball, but it creates space for someone else. That's fantastic.’ Photo: Joe Pepler