 Season 1999–00 saw Islandmagee relegated to Division 1A, but thanks to new management and virtually a whole new team, the stay below was short lived, as the Islanders bounced straight back up into the Premier section.The 2003–04 season was certainly the most successful under manager Graham McConnell, with the team reaching the semi finals of the Border Regiment and Steel & Sons cups, only to be defeated on both occasions by a strong Killyleagh side, which coincidentally knocked the team out of the Irish Cup.This Steel & Sons Cup run was particularly unique as club secretary, Crawford Wilson, was chairman of that very competition.