The 2026 summer transfer window is now officially open, with clubs able to do business.
Over the years, there have been a number of season-defining transfer windows which have heralded success - and also some absolute stinkers.
Here we rank Pompey’s last 12 summer windows, starting from the worst and finishing at the very best…
5. 9) Summer of 2020
Following another semi-final play-off defeat, this time at Oxford United in a behind-closed-doors game in the Covid era in July 2020, Jackett added Sean Raggett to the squad permanently. Money was spent on Accrington right-back Callum Johnson, while Michael Jacobs was a classy performer when injury permitted. Loanee Rasmus Nicolaisen did okay, but later flourished at Toulouse. Jordan Hiwula was a classic case of a player becoming infinitely better the longer he was out of the first-team. The reality was very different. Signings: Sean Raggett (free), Cameron Pring (loan), Callum Johnson (bought), Michael Jacobs (free), Rasmus Nicolaisen (loan), Jordy Hiwula (free).
6. 8) Summer of 2021
Now with Danny Cowley as head coach after serving as interim towards the end of the previous season in 2020-21, he oversaw the arrival of 15 new faces. Joe Morrell and Connor Ogilvie were comfortably the pick of his permanent signings and both would be integral in the 2023-24 League One title-winning season. In the case of Morrell, his career ended early following a knee injury. Gavin Bazunu and George Hirst were excellent loan recruits, blossoming with regular first-team football at Fratton Park, and would go on to play in the Premier League. However, it never quite worked out for Shaun Williams, Ryan Tunnicliffe, Jayden Reid and Kieron Freeman. While Gassan Ahadme was signed on loan off the back of a hat-trick against the Hawks, reminding us not to get carried away by a friendly performance. As for Arsenal loanee Miguel Azeez, he came with a big reputation, yet it proved to be the start of his demise. He was relegated from the National League with Morecambe last season. Signings: Liam Vincent (bought), Clarke Robertson (free), Shaun Williams (free), Ryan Tunnicliffe (free), Gavin Bazunu (loan), Kieron Freeman (free), Gassan Ahadme (loan), Jayden Reid (free), Connor Ogilvie (free), George Hirst (loan), Joe Morrell (bought), Louis Thompson (free), Miguel Azeez (loan), Mahlon Romeo (loan), Jay Mingi (free). | Jason Brown.
7. 7) Summer of 2017
Following Paul Cook’s defection to Wigan in May 2017, Kenny Jackett oversaw Pompey being back in League One and handled the accompanying transfer window. Brett Pitman and Nathan Thompson were excellent signings and, along with another summer recruit in Oli Hawkins, were part of the 2019 Checkatrade Trophy-winning team. Loanee Tareiq Holmes-Dennis sustained an injury on his debut which, ultimately, would end his career, while Dion Donohue had a classy left foot and provided the pass for Andre Green’s FA Cup at Norwich in January 2019. A fee was paid for Spurs’ Luke McGee, but it didn’t quite click for him at Fratton Park and he has subsequently spent his career largely around League One and League Two. Signings: Nathan Thompson (free), Tareiq Holmes-Dennis (loan), Luke McGee (bought), Brett Pitman (bought), Dion Donohue (bought), Oli Hawkins (bought), Damien McCrory (loan), Matty Kennedy (loan), Stuart O’Keefe (loan). | National World
8. 6) Summer of 2016
Having lost in the 2015-16 League Two play-off semi-finals to Plymouth, albeit with a side devastated by injury, Cook realised he needed to fine-tune his squad to mount another promotion challenge. Early business was promising, with the free signing captures of Danny Rose and Carl Baker proving pivotal, establishing themselves as regulars in a team which would clinch the title that season. Matt Clarke also arrived permanently, having been a makeweight in the transfer of Adam Webster to Ipswich, while Cook finally resolved his long-standing goalkeeping problem by signing David Forde on loan from Millwall. Others bolstered squad options, including Tom Davies, Amine Linganzi, Noel Hunt and, to an extent, Drew Talbot. Although Michael Clarke and Curtis Main had difficult times. Signings: Danny Rose (free), Matt Clarke (bought), Carl Baker (free), Drew Talbot (free), Michael Smith (bought), Milan Lalkovic (free), Tom Davies (free), Curtis Main (bought), David Forde (loan), Adam Buxton (free), Noel Hunt (free), Amine Linganzi (free), Liam O’Brien (free), Dominic Hyam (loan).