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.
1. Josh Passley
The right-back spent three-and-a-half months on loan from Fulham, making 12 outings. After arriving at the end of the January window in 2015, he departed April 2015 and now appears for Havant & Waterlooville. Photo: Joe Pepler
2. Conor Wilkinson
Wilkinson arrived on loan from Bolton in March 2016 but failed to register a start for the Blues. In fact, he featured just once in a 21 minute cameo off the bench on the final day of the campaign after falling out with boss Paul Cook. Photo: Joe Pepler
3. Miguel Azeez
The youngster joined from Arsenal in 2021, with plenty expecting the midfielder to impress in League One. However, he failed to live up to the hype and returned in January 2022 after just four league starts. Photo: Stephen Flynn
4. Lloyd Isgrove
The winger was one of a number of unsuccessful signings during the 2019 January window. During his six-month stay at Fratton Park, Isgrove failed to make an outing for the Blues after being continuously overlooked by Kenny Jackett. Photo: Joe Pepler