Danny Cowley welcomed four players from the first division in 2021-22, but his predecessor Kenny Jackett was no stranger to doing the same.
And with the Blues expected to explore the loan market again this summer, who can they use as a guide to finding the right fit for next season?
Many have gone on to great things at home and abroad, while others have diminished in stature.
1. George Hirst - Leicester (2021-22)
The 23-year-old impressed during his loan spell last season by scoring 13 goals in all competitions. It's expected he will return to the Foxes for pre-season but there is a desire from Danny Cowley and the player for a return to Fratton Park in before next season. The Blues may have to bide their time to get him and they will most likely have to pay a greater percentage of his wages. Picture: Jason Brown Photo: Jason Brown
2. Gavin Bazunu - Manchester City (2021-22)
The 20-year-old established himself as one of European football's hottest properties at Pompey due to his glowing performances. Since his loan came to an end he's been linked with a number of clubs across the Premier League, including Everton and Southampton, while clubs in Serie A are also reported to be interested in signing him this summer. Whoever replaces him at Fratton Park will have big boots to fill. Photo: Jason Brown
3. Miguel Azeez - Arsenal (2021-22)
The teenage midfielder appeared only 10 times for Pompey before his loan spell was cut short in January. Since his return to Arsenal he has failed to make an appearance for the senior team but has been a common feature on the Gunners' bench. As a result, he's slotted back into the under-23s where he was captain before moving to Fratton Park. Picture: Stephen Flynn/ProSportsImages Photo: Stephen Flynn
4. Gassan Ahadme - Norwich (2021-22)
Another Premier League loanee who struggled at Pompey last season, Ahadme failed to live up to the bloated expectations set upon him in pre-season. He too left in January before completing a permanent move to Burton from Norwich -- where he's scored three goals in 14 appearances since. His maiden Brewers strike came against the Blues at Fratton Park. Photo: Jason Brown