Names such as Ben Thompson, Gavin Bazunu and George Hirst spring to mind after contributing to the success at Fratton Park.
However, not all switches to the south coast have worked out, with many being forgotten by the Blues supporters.
But which have been some of the worst temporary spells at Pompey?
We’ve taken a look at the most disappointing loan moves to the Blues since their relegation from the Premier League to rediscover some of those less memorable names.
9. Paul McCallum
After arriving in January 2015, the striker picked up a red card in just his second game and was subsequently banned after making contact with referee Lee Collins. In fact, he picked up more dismissal’s than goals for the Blues, having failed to score in any of his seven substitute appearances. Photo: Joe Pepler
10. Tyler Walker
The Coventry loanee joined with plenty of promise but left with a lot of what ifs. He netted just once in 15 outings for Pompey in the second half of the 2021-22 campaign. Walker’s disappointing display against Cheltenham in April represented his final outing for the Blues and was an unused sub in their final six games of the season. Photo: Nigel Keene
11. Aaron Simpson
The right-back arrived on deadline day in January 2017 but failed to make an outing while on loan from Wolves. He returned to Molinuex at the end of the campaign and would go on to appear on ITV's Love Island in 2021. Photo: Joe Pepler
12. James Vaughan
Vaughan was another new face through the doors at PO4 in January 2019 as the former Everton striker looked to answer Kenny Jackett’s attacking issues. However, after a falling out with the Blues boss, he made just 11 outings in all competitions and just two starts in League One. Photo: Joe Pepler