In 1965/66 Glentoran ended a 15 year wait to pick up the Irish Cup crown for an 8th time, once again against the old enemy Linfield. Terry Conroy was the hero on the day, scoring both goals in a 2-0 victory. Conroy was born in Dublin and signed for Glentoran at the age of 19 following a spell with Home Farm. He signed for the Glens and went straight into the squad for the Seconds in the Steel and Sons Cup Final victory over Larne. His first team debut was a goalscoring one as he netted in a 3-2 win against Ards, a game which saw Glentoran's leading goalscorer Trevor Thompson bag his 300th for the club.
Once again Glentoran found themselves facing the old enemy in The Irish Cup Final, as the packed Oval hosted Linfield on 23rd April. The game marked the opening of the lower stand, adding 1,100 additional seats to the 2,500 upstairs. The day will be sadly remembered for an incident where a group of Linfield supporters hit Glentoran keeper Albert Finlay in the groin with a stone but following treatment, Finlay played on. Glentoran got their revenge too running out 2-0 winners. Terry Conroy was the hero with both goals scored on the 32nd and 88th minute.
Conroy scored 8 goals in that first season for Glentoran and impressed in the next season, the 66-67 season, possibly the most famous in Glentoran's history. Conroy scored 25 goals and took part in the famous draw over Rangers in the Cup Winners Cup. His impressive performances saw him secure a move in March 1967 to Stoke for a reported £15,000. Sadly a March departure meant Conroy missed out on the famous Detroit Cougar tour that summer but Conroy still played his part in arguably Glentoran's greatest ever side.
But for Glentoran it will be those two goals over Linfield that ended a 15 year wait for an Irish Cup crown that have earned him a deserved spot on Glentoran's Cup Final Hero list.