Joe Oastler suffered play-off heartbreak after Torquay lost 1-0 against Stevenage.
Old Trafford provided the setting for the League Two final on Saturday.
And Stevenage ran out 1-0 winners thanks to John Mousinho’s decisive goal in the 41st minute.
For Graham Westley’s side – who Pompey played in the Carling Cup this season – it marked back-to-back promotions.
Yet it was agony for ex-Pompey youngster Oastler, who has spent the season on loan with Torquay from QPR.
The 20-year-old from Milton had been an integral part of the Gulls side which reached the play-offs, making 31 appearances.
He was a substitute on Saturday, entering the fray in the 79th minute.
Within 70 seconds, the midfielder was booked following a late lunge on Stevenage’s Byron Harrison.
However, his introduction failed to inspire Paul Buckle’s men as they could find no late rally.
Nonetheless, it has still been a remarkable season for Oastler, a long-time Pompey team-mate of fellow local starlets Joel Ward and Matt Ritchie, who was released in 2008.
Out of contract with QPR this summer, he has already held talks over staying at the Gulls permanently following an impressive campaign.
Other clubs have also shown interest in the former East Lodge footballer, who owned a Fratton Park season ticket until the age of 16.
Oastler’s future appears bright as he attempts to prove Paul Hart wrong in showing him the Pompey door three years ago.
In the meantime, Torquay face another season in League Two following that devastating defeat.
They are also waiting nervously waiting on the future of manager Buckle, who has refused to rule out taking over managerless Bristol Rovers.
The Old Trafford match saw Stevenage dominate the first half, with the lively Darius Charles heading over and wide.
The Gulls improved after the break and Jake Robinson came close, hitting the bar from 20 yards.
The fact the two teams were Blue Square Premier rivals two years ago demonstrated the ever-narrowing gap between the top non-league teams and the bottom tier of the Football League.
And Westley’s side, in their first season of being a league team following last season’s promotion from the Blue Square Bet Premier, repeated Exeter’s feat of double promotions to the third tier in 2008 and 2009.