But as we wait for number 23 to arrive, with Josh Griffiths edging closer to a Fratton Park switch, we’ve decided to take a look back at the players the Blues manager has turned to in a bid to achieve success on the south coast – and offered an opinion on whether they are or have been a hit or a miss.
Here’s the judgement we’ve made, with emergency keeper Jake Eastwood not included given the very brief period he spent on loan from Sheffield United.
1. Ryan Tunnicliffe
Arrived on a free transfer from Luton and immediately made an impression with a goal and three assists in his first three games. A hamstring injury slowed his progress, though, while the midfield partnership that Joe Morrell and Louis Thompson developed over the second half of the season did Tunnicliffe no favours either. Still remained a valuable player but did he help take Pompey to new heights or improve the Blues' lot following last summer's clear out? In truth, the answer has to be no.
Photo: Jacques Feeney
2. Kieron Freeman
Like Ryan Tunnicliffe, the defender arrived at a time when Pompey needed bodies to fill the void left by a player overhaul. He came with a decent record and good track record but was soon playing second fiddle to Mahlon Romeo. Injury got in the way when Romeo's form died off after the turn of the year. The jury is still out on the former Sheffield United player who has been linked with a move away this simmer. But in terms of how his first season back at Fratton Park went, there can only be one conclusion.
Photo: Graham Hunt
3. Shaun Williams
Despite picking up a serious back injury in January, the midfielder played 35 times for Pompey last season following his free transfer move from Millwall. Cowley knew exactly what he was getting from the no-frills 35-year-old when he signed him on a one-year deal. And despite ridicule from sections of the Fratton faithful, he didn't let the manager down - even playing at centre-half on occasions. Williams wasn't signed to be the star man in the middle of the park and did what was asked of him.
Photo: Jason Brown
4. Joe Morrell
Even though the Wales international's form dipped at times last season, he still proved a key player under Danny Cowley. His partnership with Louis Thompson flourished over the second half of the season and it's exciting to see how he will gel with Marlon Pack next term.
Photo: Jason Brown