| West Indies in New Zealand: 2nd Test, 1999/00 | Basin Reserve, Wellington | New Zealand won by an innings and 105 runs | 26, 27, 28, 29 December 1999 (five-day match) |
| West Indies in New Zealand: 1st Test, 1999/00 | WestpacTrust Park, Hamilton | New Zealand won by 9 wickets | 16, 17, 18, 19, 20 December 1999 (five-day match) |
| Coca-Cola Champions Trophy: 6th Match, 1999/00 | Sharjah C.A. Stadium | Pakistan won by 138 runs | 19 October 1999 |
| Coca-Cola Champions Trophy: 4th Match, 1999/00 | Sharjah C.A. Stadium | Sri Lanka won by 9 wickets | 17 October 1999 |
| Coca-Cola Champions Trophy: 2nd Match, 1999/00 | Sharjah C.A. Stadium | Pakistan won by 130 runs | 14 October 1999 |
| Coca-Cola Champions Trophy: 1st Match, 1999/00 | Sharjah C.A. Stadium | West Indies won by 3 wickets | 13 October 1999 |
| West Indies in Bangladesh: 2nd ODI, 1999/00 | Bangabandhu National Stadium, Dhaka | West Indies won by 109 runs | 9 October 1999 |
| West Indies in Bangladesh: 1st ODI, 1999/00 | Bangabandhu National Stadium, Dhaka | West Indies won by 73 runs | 8 October 1999 |
| DMC Trophy: 3rd ODI, 1999 | Toronto Cricket, Skating and Curling Club | Pakistan won by 7 wickets | 19 September 1999 |
| DMC Trophy: 2nd ODI, 1999 | Toronto Cricket, Skating and Curling Club | Pakistan won by 42 runs | 18 September 1999 |
| DMC Trophy: 1st ODI, 1999 | Toronto Cricket, Skating and Curling Club | Pakistan won by 15 runs | 16 September 1999 |
| DMC Cup: 3rd ODI, 1999 | Toronto Cricket, Skating and Curling Club | India won by 88 runs | 14 September 1999 |
| DMC Cup: 2nd ODI, 1999 | Toronto Cricket, Skating and Curling Club | West Indies won by 70 runs | 12 September 1999 |
| DMC Cup: 1st ODI, 1999 | Toronto Cricket, Skating and Curling Club | India won by 8 wickets | 11 September 1999 |
| Coca-Cola Singapore Challenge: Only Final, 1999 | Kallang Ground, Singapore | West Indies won by 4 wickets | 8 September 1999 |
| Coca-Cola Singapore Challenge: Only Final, 1999 | Kallang Ground, Singapore | No result | 7 September 1999 |
| Coca-Cola Singapore Challenge: 3rd Match, 1999 | Kallang Ground, Singapore | West Indies won by 42 runs | 5 September 1999 |
| Coca-Cola Singapore Challenge: 1st Match, 1999 | Kallang Ground, Singapore | West Indies won by 6 wickets | 2 September 1999 |
| ICC World Cup: 28th Match, 1999 | Old Trafford, Manchester | Australia won by 6 wickets | 30 May 1999 |
| ICC World Cup: 23rd Match, 1999 | Grace Road, Leicester | West Indies won by 8 wickets | 27 May 1999 |
| ICC World Cup: 18th Match, 1999 | County Ground, Southampton | West Indies won by 7 wickets | 24 May 1999 |
| ICC World Cup: 12th Match, 1999 | Castle Avenue, Dublin | West Indies won by 7 wickets | 21 May 1999 |
| ICC World Cup: 5th Match, 1999 | County Ground, Bristol | Pakistan won by 27 runs | 16 May 1999 |
| Australia in West Indies: 7th ODI, 1998/99 | Kensington Oval, Bridgetown, Barbados | West Indies won by 8 wickets by D/L method | 25 April 1999 |
| Australia in West Indies: 6th ODI, 1998/99 | Kensington Oval, Bridgetown, Barbados | Australia won by 4 wickets | 24 April 1999 |
| Australia in West Indies: 5th ODI, 1998/99 | Bourda, Georgetown, Guyana | Match Tied | 21 April 1999 |
| Australia in West Indies: 4th ODI, 1998/99 | Queen's Park Oval, Port of Spain, Trinidad | Australia won by 20 runs | 18 April 1999 |
| Australia in West Indies: 3rd ODI, 1998/99 | Queen's Park Oval, Port of Spain, Trinidad | West Indies won by 5 wickets | 17 April 1999 |
| Australia in West Indies: 2nd ODI, 1998/99 | Queen's Park (New), St George's, Grenada | Australia won by 46 runs | 14 April 1999 |
| Australia in West Indies: 1st ODI, 1998/99 | Arnos Vale Ground, Kingstown, St Vincent | West Indies won by 44 runs | 11 April 1999 |
| The Frank Worrell Trophy: 4th Test, 1998/99 | Antigua Recreation Ground, St John's, Antigua | Australia won by 176 runs | 3, 4, 5, 6, 7 April 1999 (five-day match) |
| The Frank Worrell Trophy: 3rd Test, 1998/99 | Kensington Oval, Bridgetown, Barbados | West Indies won by 1 wickets | 26, 27, 28, 29, 30 March 1999 (five-day match) |
| The Frank Worrell Trophy: 2nd Test, 1998/99 | Sabina Park, Kingston, Jamaica | West Indies won by 10 wickets | 13, 14, 15, 16 March 1999 (five-day match) |
| The Frank Worrell Trophy: 1st Test, 1998/99 | Queen's Park Oval, Port of Spain, Trinidad | Australia won by 312 runs | 5, 6, 7, 8 March 1999 (five-day match) |
| West Indies in South Africa: 7th ODI, 1998/99 | SuperSport Park, Centurion | South Africa won by 50 runs | 7 February 1999 |
| West Indies in South Africa: 6th ODI, 1998/99 | Springbok Park, Bloemfontein | South Africa won by 114 runs | 5 February 1999 |
| West Indies in South Africa: 5th ODI, 1998/99 | Newlands, Cape Town | South Africa won by 89 runs | 2 February 1999 |
| West Indies in South Africa: 4th ODI, 1998/99 | Crusaders Ground, St George's Park, Port Elizabeth | South Africa won by 99 runs | 30 January 1999 |
| West Indies in South Africa: 3rd ODI, 1998/99 | Kingsmead, Durban | South Africa won by 55 runs | 27 January 1999 |
| West Indies in South Africa: 2nd ODI, 1998/99 | Buffalo Park, East London | West Indies won by 43 runs | 24 January 1999 |
| West Indies in South Africa: 1st ODI, 1998/99 | New Wanderers Stadium, Johannesburg | South Africa won by 2 wickets by D/L method | 22 January 1999 |
| West Indies in South Africa: 5th Test, 1998/99 | Centurion Park | South Africa won by 351 runs | 15, 16, 17, 18 January 1999 (five-day match) |
| West Indies in South Africa: 4th Test, 1998/99 | Newlands, Cape Town | South Africa won by 149 runs | 2, 3, 4, 5, 6 January 1999 (five-day match) |
