Gaels reached the final of the Ulster Senior Club Football Championship twice during this period, losing to Crossmaglen Rangers in 1999 and to Errigal Ciarán in 2002.

[1][2] The bid for seven championships in a row was ended by Derrygonnelly Harps in the 2004 county final.

[5] Backboned by the 2017 Ulster Minor winning team,[6] the club would claim the Fermanagh Intermediate crown in 2020.

[8] A youthful Gaels team lost by nine points to Derrygonnelly.

Enniskillen were comfortable winners and ended a 16-year wait for the New York Cup.