Forgotten Danny Cowley signing denied Portsmouth reunion as pre-season plans take shape
Ollie Webber never played for Pompey during his six-month stay at Fratton Park.
Pompey announced the first stages of their Championship preparations on Thursday evening as excitement builds ahead of the new season.
The Blues confirmed a week-long training camp in Slovakia will be first on the agenda for John Mousinho’s men, who return to training on June 23rd.
After that, fixtures against Farnborough, Woking, Hawks and Crawley will take place, while further additions to the schedule will be revealed closer to the time.
However, there will be no customary visit to Gosport or Bognor this season, with the traditional summer friendlies forced to be scrapped.
This will pave the way for a first pre-season trip to Woking in six years, with the Blues’ last visit to the Kingfield Stadium coming in a 4-2 triumph in 2019.
Forgotten Pompey signing to miss Blues reunion
However, one former Fratton Park goalkeeper has been denied a Pompey reunion ahead of July’s meeting.
Forgotten Danny Cowley signing Ollie Webber spent the 2024-25 campaign with the Cards, registering just three appearances.
Despite being second-choice behind number one Will Jaaskelainan, the Portsmouth-born stopper started the final two games of the campaign for Neil Ardley’s men, who finished 15th in the National League.
But it wasn’t enough to convince the former AFC Wimbledon boss to renew his terms with the club and was released along with 10 other first-team members.
Webber spent just one season with Woking after signing from Northern Ireland side Glentoran last summer. His departure now rules out any hope of reuniting with the Blues following his exit three years ago.
The 24-year-old arrived at Fratton Park in January 2022, penning a deal until the end of the 2021-22 campaign. This was to allow second-choice Alex Bass to join Bradford City on loan after Gavin Bazunu nailed down the number one shirt.
The Northern Ireland youth international, though, would never play for Pompey during his five-month stint at PO4 and was instead named on the bench on 20 occasions.
Following the Blues’ 10th-placed finish, Webber was released by Cowley along with Shaun Williams, Paul Downing, Callum Johnson and Aiden O’Brien.
He would return to his native Northern Ireland that summer, where he joined Glentoran on a two-year deal. The Crystal Palace youth product registered just 10 appearances, however, before his 2024 exit.
Pompey to face familiar figure in pre-season friendly

Pompey will, though, line-up against a more familiar face when they face Woking in July, with former interim boss and coach Simon Bassey among Ardley’s backroom staff.
The 49-year-old worked under the head coach during a successful spell with AFC Wimbledon, which saw them win promotion to League One in 2016.
Bassey spent 18 months at Fratton Park, joining Cowley’s coaching department in June 2021.
The former Aldershot and Crawley midfielder was then placed in caretaker charge following the Blues boss’ sacking in January 2023 and led Pompey out against Spurs in the FA Cup third-round tie.
However, he would not remain as part of Mousinho’s backroom and departed later that month. team Bassey joined Woking in December and helped steer the Cards away from relegation and into 15th.
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