The 2008–09 season was one of mixed fortunes for Kilmore Rec. They managed to make it to the Border Cup Final for a third time, only to taste defeat for a third time, when Sport and Leisure ran out 3–1 winners. Gary Kennedy got the Kilmore goal with a blistering free kick. Kilmore's league form suffered due to their run in the Border Cup and subsequent loss. League leaders Abbey Villa had already gained significant progress and Kilmore were to play catchup for the remainder of the season. In a tightly fought race for second, Kilmore finished the season 4th, behind Ards Rangers and Sport and Leisure with only four points separating Kilmore and 2nd place Ards Rangers.