For Pompey’s opening game in the competition at Crawley, only Ronan Curtis started the league match against Port Vale three days earlier.
And that type of rotation is expected again as Cowley looks to get minutes into the legs of those who have been on the fringes in recent fixtures.
Several of the club’s academy youngsters could also be called upon to make up the numbers.
So who will the manager be turning to for tonight’s fixture?
Here’s how we think the Blues could line up.
9. Michael Jacobs
Despite making 10 appearances this season, the popular forward has had a relatively quiet start to this season. And with the Blues' other attacking players all playing to decent standards this term, there's been no overriding calls to get Jacobs - who has just four league starts to date - back into the team on a regular basis. He needs to remind fans what he is capable of - and tonight should provide him with that platform. Photo: Jason Brown
10. Joe Pigott
Danny Cowley loves having the on-loan Ipswich striker in his ranks and feels for the front man as fellow strikers Colby Bishop and Dane Scarlett keep producing the goods on a regular basis. He scored a hat-trick in the recent behind-closed-doors friendly win against Chelsea before sitting out the trip to Portman Road. Will be itching to play tonight and give Cowley a reminder of his goalscoring talent. Photo: Jason Brown
11. Ronan Curtis
The Irishman has featured in all 13 games of Pompey's season to date - and that is likely to continue tonight after being left out of the starting XI for the trip to Ipswich. Despite four goals and four assists in those games, Curtis will feel he has a point to prove again with the manager - although could very well start up front tonight with Pigott. Photo: Jason Brown