Together with Jimmy McGeough, Jim Crossan and Matt Doherty, Gilbert was a member of the Derry City team that overcame F.C.
However, he missed the return leg on 9 September because of injury, but Gilbert's two goals helped City to an 8–6 aggregate win.
Together with Liam Tuohy, Johnny Fullam, Pat Dunne, Frank O'Neill, Mick Leech and Paddy Mulligan, Gilbert was a prominent member of the Rovers team that dominated the FAI Cup during the 1960s.
After holding Bayern to a 1–1 draw at Dalymount Park, goals from Gilbert and Liam Tuohy saw Rovers came back from 2–0 down during the away game.
[7] On 4 May 1966, while playing for Shamrock Rovers, Gilbert made his one and only appearance the Republic of Ireland in friendly against West Germany at Dalymount Park.