'Absolutely dreadful, Won the league, Inspired recruitment': Portsmouth's last 12 summer transfer windows ranked

Chief sports writer

Published 15th Jun 2026, 18:00 BST

Updated 15th Jun 2026, 18:31 BST

We rank every Pompey summer transfer window since 2014 - the good, the bad and the ugly

The 2026 summer transfer window is now officially open, with clubs able to do business.

As ever, Pompey expect to be busy as they strive to evolve from being regular relegation battlers into a comfortable mid-table Championship existence at the very least.

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…

Enda Stevens, Kyle Bennett and Michael Doyle all joined Pompey in the summer on 2015.

1. Enda Stevens, Kyle Bennett and Michael Doyle all joined Pompey in the summer on 2015.

Enda Stevens, Kyle Bennett and Michael Doyle all joined Pompey in the summer on 2015. | Bluepitch Media / Joe Pepler

Having kept Pompey in the Football League, Andy Awford was rewarded with the Pompey job on a permanent basis and set about stamping his mark on the squad.

Danny Hollands was signed from Charlton, having impressed on loan at the tail-end of the previous season, while centre-half Paul Robinson’s loan arrival from Millwall was excellent business.

For the first time since emerging from administration, Pompey were also able to pay transfer fees, with Nigel Atangana and James Dunne recruited for money. In addition, goalkeeper Paul Jones was a solid signing.

However, Craig Westcarr won’t be fondly remembered, while Alex Wynter was a poor loan signing from Crystal Palace.

Overall, an absolutely dreadful window which heralded 16th place in League Two - Pompey's worst Football League finish in their history.

Signings: Danny Hollands (free) Paul Jones (free), Craig Westcarr (free), Nigel Atangana (bought), Michael Poke (free), James Dunne (bought), Alex Wynter (loan), Miles Storey (loan), Paul Robinson (loan), Peter Brezovan (free).

2. 12) Summer of 2014

Having kept Pompey in the Football League, Andy Awford was rewarded with the Pompey job on a permanent basis and set about stamping his mark on the squad. Danny Hollands was signed from Charlton, having impressed on loan at the tail-end of the previous season, while centre-half Paul Robinson’s loan arrival from Millwall was excellent business. For the first time since emerging from administration, Pompey were also able to pay transfer fees, with Nigel Atangana and James Dunne recruited for money. In addition, goalkeeper Paul Jones was a solid signing. However, Craig Westcarr won’t be fondly remembered, while Alex Wynter was a poor loan signing from Crystal Palace. Overall, an absolutely dreadful window which heralded 16th place in League Two - Pompey's worst Football League finish in their history. Signings: Danny Hollands (free) Paul Jones (free), Craig Westcarr (free), Nigel Atangana (bought), Michael Poke (free), James Dunne (bought), Alex Wynter (loan), Miles Storey (loan), Paul Robinson (loan), Peter Brezovan (free). | Bluepitch Media / Joe Pepler

Buoyed by an outstanding second half to the 2024-25 season as Pompey transformed themselves from relegation certainties to surviving with two matches to spare, Mousinho and Co set about strengthening the squad.

The first signing was Adrian Segecic from Sydney, representing the perfect start to the transfer window, yet that was as good as it got for the Blues.

Josef Bursik deserves credit, looking a quality goalkeeper in his 11 outings, primarily when Nicolas Schmid was injured. Blues fans certainly feel more comfortable with Bursik than Ben Killip as back-up.

Mark Kosznovszky’s season ended in December through injury, Minhyeok Yang was recalled by Spurs, Josh Knight was underwhelming and never played after November following a serious back injury.

Conor Chaplin’s arrival was warmly received by everyone, but disappointingly it never worked out, while John Swift has also yet to live up to his billing, finding himself in and out of the side, often in playing positions which don’t suit him.

As for Florian Bianchini, Swansea didn’t even want him back in January, refusing to consider cancelling his loan, despite injury and struggling for selection even when fit.

Signings: Adrian Segecic (bought), John Swift (free), Mark Kosznovszky (bought), Luke Le Roux (bought), Florian Bianchini (loan), Minhyeok Yang (loan), Josh Knight (bought), Josef Bursik (bought), Makenzie Kirk (bought), Franco Umeh (bought), Conor Chaplin (loan).

3. 11) Summer of 2025

Buoyed by an outstanding second half to the 2024-25 season as Pompey transformed themselves from relegation certainties to surviving with two matches to spare, Mousinho and Co set about strengthening the squad. The first signing was Adrian Segecic from Sydney, representing the perfect start to the transfer window, yet that was as good as it got for the Blues. Josef Bursik deserves credit, looking a quality goalkeeper in his 11 outings, primarily when Nicolas Schmid was injured. Blues fans certainly feel more comfortable with Bursik than Ben Killip as back-up. Mark Kosznovszky’s season ended in December through injury, Minhyeok Yang was recalled by Spurs, Josh Knight was underwhelming and never played after November following a serious back injury. Conor Chaplin’s arrival was warmly received by everyone, but disappointingly it never worked out, while John Swift has also yet to live up to his billing, finding himself in and out of the side, often in playing positions which don’t suit him. As for Florian Bianchini, Swansea didn’t even want him back in January, refusing to consider cancelling his loan, despite injury and struggling for selection even when fit. Signings: Adrian Segecic (bought), John Swift (free), Mark Kosznovszky (bought), Luke Le Roux (bought), Florian Bianchini (loan), Minhyeok Yang (loan), Josh Knight (bought), Josef Bursik (bought), Makenzie Kirk (bought), Franco Umeh (bought), Conor Chaplin (loan). | Dennis Goodwin

Reeling from the agony of losing in the 2018-19 League One play-off semi-finals to Sunderland, Kenny Jackett went out to strengthen his side.

Buoyed by a transfer war chest following the sales of Jamal Lowe and Matt Clarke, Pompey’s boss splashed out on Marcus Harness, Ellis Harrison and John Marquis. Only Harness could be considered value for money.

Initially a loanee, Sean Raggett suffered a slow start, before establishing himself as a player who would become a cult figure over the next five seasons.

There was also the return of former Academy player Ryan Williams, while Rangers loanee Ross McCrorie did okay, albeit only after being converted to a right-back. Paul Downing didn’t.

Signings: James Bolton (free), Ellis Harrison (bought), Paul Downing (free), Ryan Williams (free), Sean Raggett (loan), Ross McCrorie (loan), Marcus Harness (bought), John Marquis (bought)

4. 10) Summer of 2019

Reeling from the agony of losing in the 2018-19 League One play-off semi-finals to Sunderland, Kenny Jackett went out to strengthen his side. Buoyed by a transfer war chest following the sales of Jamal Lowe and Matt Clarke, Pompey’s boss splashed out on Marcus Harness, Ellis Harrison and John Marquis. Only Harness could be considered value for money. Initially a loanee, Sean Raggett suffered a slow start, before establishing himself as a player who would become a cult figure over the next five seasons. There was also the return of former Academy player Ryan Williams, while Rangers loanee Ross McCrorie did okay, albeit only after being converted to a right-back. Paul Downing didn’t. Signings: James Bolton (free), Ellis Harrison (bought), Paul Downing (free), Ryan Williams (free), Sean Raggett (loan), Ross McCrorie (loan), Marcus Harness (bought), John Marquis (bought)