During the past three winter windows, the Blues have been unable to add the necessary players required to deliver League One promotion.
Pompey were sixth on New Year's Day during Jackett’s first season in charge in 2017-18 but would go on to finish eighth.
They sat top at the turn of the year the following campaign but dropped to fourth and suffered play-off semi-final defeat to Sunderland.
And while the Blues moved up from ninth to fifth last term, they again lost in the play-offs to Oxford on penalties.
It total, Kenny Jackett had made 13 signings in the past three January windows.
In truth, the majority of the players recruited haven’t worked out at Fratton Park.
There have been a few who’ve impressed, however, while one signing is very much for the future.
We’ve had a go at ranking those who’ve arrived midway through the season – from worst to best. Scroll down to see our list…
13. 1) Andy Cannon
The midfielder was the first player through the door in January 2019, signing for a fee of £150,000 from Rochdale. Cannon was hampered by injury in his first season but has become a key player at PO4 - especially this season. He's fundamental in the engine room and somone Pompey will want to keep beyond his contract this summer. In total, Cannon's made 53 appearances, scoring once. Photo: Joe Pepler