The Australian cricket team toured the Caribbean from February to April 1999 to play four Tests and seven One Day Internationals (ODIs) against the West Indies.

Australia's Test captain Mark Taylor initially indicated that he would continue to lead the side for this tour,[15] but in February 1999 he announced his retirement.

[16][17] Steve Waugh, who had held the captaincy of the ODI side for 18 months, was appointed as the new Test captain with Shane Warne as his deputy.

[18] Conversely, the West Indies on their first tour of South Africa in the post-apartheid era had suffered their first 5–0 Test whitewash and lost the ODI series 6–1.

[14][19] Brian Lara led a player revolt against the WICB over pay and conditions and the tour was delayed by a week.

[33] Lara was rested due to a wrist injury for the final three matches with Jimmy Adams standing in as captain.

[37] The final ODI match was suspended for over an hour due to spectators throwing glass bottles and other debris onto the ground in protest at Sherwin Campbell being obstructed by Brendon Julian and being given run out.

Midway through the final day's play, the crowd threw bottles onto the ground after the controversial lbw dismissal of Roy Fredericks.

[41] Prior to the final ODI match, the former West Indian captain Carl Hooper announced his retirement from international cricket.

[54] The thirteen man squad announced ahead of the third Test saw Adrian Griffith, Carl Hooper and Shivnarine Chanderpaul coming in as replacements for Suruj Ragoonath, Daren Ganga and Lincoln Roberts.