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.
13. Sylvain Deslandes
Deslandes was another failed loanee from Wolves as he joined alongside Conor Ronan in January 2018. He made just two outings for the Blues but his underwhelming displays saw him never appear under Jackett again at Fratton Park, Photo: Joe Pepler
14. Alex Wynter
The then young defender made the season-long switch to Fratton Park from Crystal Palace in the summer of 2014. However, Wynter made just 15 outings in all competitions and was subsequently recalled six-months later in January. Photo: Joe Pepler
15. Ibrahima Sonko
The defender was the first arrival through the doors at PO4 following their relegation from the Premier League in 2010. After joining on a season-long loan, he made just 22 league outings for the Blues and would depart in May 2011. Photo: Barry Zee