The ex-Cardiff midfielder returned to his boyhood club to pen a two-year deal at Fratton Park.
Yet, that deal remains the only signing for the Blues to date.
Trio Kieron Freeman, Marcus Harness and Ronan Curtis have all been linked with moves away this summer but remain part of the group as Pompey up their preparations for the new season.
Pompey make the annual trip to Westleigh Park on Saturday for their first pre-season fixture but what would their strongest side look like if the season started tomorrow?
We’ve taken a look at the best starting XI Cowley could name if that was the case.
Here’s how we think they would line up.