Portsmouth to face former boss and familiar faces as Trophy details are confirmed

The Blues have been matched up with Gillingham and League One new boys Leyton Orient in next season’s competition.

The meeting with the Gills means John Mousinho’s men could go up against some familiar faces.

Former Pompey players Oli Hawkins and Shaun Williams are are both contracted at Priestfield next term, while keeper Glenn Morris spent a short period on trial in 2012.

Ex-Blues favourite Aiden O’Brien spent the second half of the season on loan in Kent from Shrewsbury, while former midfielder Stuart O’Keefe was released last month.

It’s the presence of Jackett, however, who is now director of football at the club which adds some intrigue to the clash.

Jackett, of course, spent four years at Fratton Park - twice leading his side to the play-offs before coming up short on both occasions.

The 61-year-old memorably won the Trophy against Sunderland in 2019, but was sacked after a defeat to Salford at the final stage two years ago.

Owner Brad Galinson is showing ambition at Gillingham, with the club bringing in Wales international Jonny Williams this summer.

Pompey will face another another of Jackett’s old clubs in Orient - who stormed to the League Two crown under Richie Wellens last season, finishing six points clear of Stevenage.

The Blues will compete against those sides in Group E, with the group completed by an invited club.

That will be one of Arsenal, Aston Villa, Brighton, Chelsea, Crystal Palace, Fulham, Spurs or West Ham’s under-21 sides.

Those details are expected to be confirmed tomorrow, which is when the League One fixtures will be released.

Mousinho’s men will also find out their Carabao Cup opponents. They will be ball number 25 in the regionalised draw.