A bumper Pompey crowd turned out to pay tribute to Hermann Hreidarsson - and raise funds for the Trust.
The Blues beat IBV 2-1 in a friendly through goals from Bradley Tarbuck and Liam Walker.
Kjartan Gudjonsson pulled one back in stoppage time to give the scoreline a closer feel but the occasion was not about the result.
An attendance of 6,780 fans at Fratton Park witnessed the fixture, which also saw a few faces from the past granted cameos.
Manager-to-be Guy Whittingham, Linvoy Primus, Svetoslav Todorov and Mark Kelly appeared from the last 11 minutes amid massive receptions.
Hreidarsson was already on the pitch at that stage as a second-half substitute for IBV, although David James did not play despite being present.
The Hermannator played the final few minutes for Pompey, an appropriate end to the career of a Fratton hero who left the field to familiar renditions of ‘Hermann Hreidarsson’ ringing out.