← 1999 Leeward Islands Championship Qualifying

Nov. 6, 1999 1999 British Virgin Islands 2 - 2 Nevis Nevis 1
Nov. 8, 1999 1999 British Virgin Islands 2 - 0 Nevis British Virgin Islands 1
Nov. 14, 1999 1999 British Virgin Islands 2 - 3 Saint Croix Antigua and Barbuda 1