| 26 Dec 1999 | NZ 518/9 v WI 179/9 & 234/92nd Test · Test | WI | 67 & 75 | - | 0 | New Zealand won by an innings and 105 runs | Wellington | West Indies tour of New Zealand 1999/00 |
| 16 Dec 1999 | WI 365 & 97 v NZ 393 & 70/11st Test · Test | WI | 24 & 1 | - | 0 | New Zealand won by 9 wickets | Hamilton | West Indies tour of New Zealand 1999/00 |
| 19 Oct 1999 | PAK 255/5 v WI 1176th Match · ODI | WI | 30 | - | 0 | Pakistan won by 138 runs | Sharjah | Coca Cola Champions Trophy 1999/00 |
| 17 Oct 1999 | WI 145 v SL 146/14th Match · ODI | WI | 29 | - | 0 | Sri Lanka won by 9 wickets (with 132 balls remaining) | Sharjah | Coca Cola Champions Trophy 1999/00 |
| 14 Oct 1999 | PAK 260/5 v WI 130/92nd Match · ODI | WI | 8 | - | 1 | Pakistan won by 130 runs | Sharjah | Coca Cola Champions Trophy 1999/00 |
| 13 Oct 1999 | SL 178 v WI 181/71st Match · ODI | WI | 0 | - | 0 | West Indies won by 3 wickets (with 4 balls remaining) | Sharjah | Coca Cola Champions Trophy 1999/00 |
| 9 Oct 1999 | WI 314/6 v BAN 2052nd ODI · ODI | WI | 117 | 2/12 | 0 | West Indies won by 109 runs | Dhaka | West Indies tour of Bangladesh 1999/00 |
| 19 Sept 1999 | WI 161 v PAK 162/33rd ODI · ODI | WI | 12 | - | 0 | Pakistan won by 7 wickets (with 62 balls remaining) | Toronto | Pakistan tour of Canada 1999 |
| 16 Sept 1999 | PAK 230/6 v WI 215/91st ODI · ODI | WI | 20 | - | 0 | Pakistan won by 15 runs | Toronto | Pakistan tour of Canada 1999 |
| 14 Sept 1999 | IND 225/7 v WI 1373rd ODI · ODI | WI | 26 | - | 1 | India won by 88 runs | Toronto | 1999 Singapore Challenge |
| 12 Sept 1999 | WI 190/6 v IND 1202nd ODI · ODI | WI | 34 | - | 0 | West Indies won by 70 runs | Toronto | 1999 Singapore Challenge |
| 8 Sept 1999 | IND 254/6 v WI 255/6Final · ODI | WI | 18 | - | 1 | West Indies won by 4 wickets (with 14 balls remaining) | Singapore | 1999 Singapore Challenge |
| 5 Sept 1999 | IND 154/8 v WI 196/73rd Match · ODI | WI | 60 | - | 0 | West Indies won by 42 runs | Singapore | 1999 Singapore Challenge |
| 2 Sept 1999 | WI 247/4 v ZIM 244/91st Match · ODI | WI | 48 | - | 1 | West Indies won by 6 wickets (with 38 balls remaining) | Singapore | 1999 Singapore Challenge |
| 30 May 1999 | AUS 111/4 v WI 11028th Match · ODI | WI | 9 | - | 0 | Australia won by 6 wickets (with 56 balls remaining) | Manchester | 1999 Cricket World Cup |
| 27 May 1999 | SCO 68 v WI 70/223rd Match · ODI | WI | 25* | - | 0 | West Indies won by 8 wickets (with 239 balls remaining) | Leicester | 1999 Cricket World Cup |
| 24 May 1999 | NZ 156 v WI 158/318th Match · ODI | WI | 36 | - | 2 | West Indies won by 7 wickets (with 34 balls remaining) | Southampton | 1999 Cricket World Cup |
| 21 May 1999 | BAN 182 v WI 183/312th Match · ODI | WI | 25 | - | 2 | West Indies won by 7 wickets (with 21 balls remaining) | Dublin | 1999 Cricket World Cup |
| 16 May 1999 | PAK 229/8 v WI 2025th Match · ODI | WI | 11 | - | 1 | Pakistan won by 27 runs | Bristol | 1999 Cricket World Cup |
| 18 Apr 1999 | WI 169 v AUS 189/94th ODI · ODI | WI | 6 | - | 0 | Australia won by 20 runs | Port of Spain | Australia tour of West Indies 1998/99 |
| 17 Apr 1999 | WI 244/5 v AUS 242/73rd ODI · ODI | WI | 18* | - | 0 | West Indies won by 5 wickets (with 6 balls remaining) | Port of Spain | Australia tour of West Indies 1998/99 |
| 14 Apr 1999 | WI 242 v AUS 288/42nd ODI · ODI | WI | 9 | - | 1 | Australia won by 46 runs | St. George's | Australia tour of West Indies 1998/99 |
| 11 Apr 1999 | WI 209 v AUS 1651st ODI · ODI | WI | 16 | - | 0 | West Indies won by 44 runs | Kingstown | Australia tour of West Indies 1998/99 |
| 3 Apr 1999 | WI 222 & 211 v AUS 303 & 3064th Test · Test | WI | 100 & 7 | - | 1 | Australia won by 176 runs | St. John's | Australia tour of West Indies 1998/99 |
| 26 Mar 1999 | WI 329 & 311/9 v AUS 490 & 1463rd Test · Test | WI | 8 & 153* | - | 2 | West Indies won by 1 wicket | Bridgetown | Australia tour of West Indies 1998/99 |
| 13 Mar 1999 | WI 431 & 3/0 v AUS 256 & 1772nd Test · Test | WI | 213 & DNB | - | 2 | West Indies won by 10 wickets | Kingston | Australia tour of West Indies 1998/99 |
| 5 Mar 1999 | WI 167 & 51 v AUS 269 & 2611st Test · Test | WI | 62 & 3 | - | 1 | Australia won by 312 runs | Port of Spain | Australia tour of West Indies 1998/99 |
| 7 Feb 1999 | SA 226/8 v WI 1767th ODI · ODI | WI | 9 | - | 0 | South Africa won by 50 runs | Centurion | West Indies tour of South Africa 1998/99 |
| 27 Jan 1999 | SA 274/9 v WI 2193rd ODI · ODI | WI | 32 | - | 1 | South Africa won by 55 runs | Durban | West Indies tour of South Africa 1998/99 |
| 24 Jan 1999 | SA 249 v WI 292/92nd ODI · ODI | WI | 3 | - | 0 | West Indies won by 43 runs | East London | West Indies tour of South Africa 1998/99 |
| 22 Jan 1999 | SA 160/8 v WI 154/41st ODI · ODI | WI | 0 | - | 0 | South Africa won by 2 wickets (with 0 balls remaining) (D/L method) | Johannesburg | West Indies tour of South Africa 1998/99 |
| 15 Jan 1999 | SA 313 & 399/5 v WI 144 & 2175th Test · Test | WI | 68 & 14 | - | 2 | South Africa won by 351 runs | Centurion | West Indies tour of South Africa 1998/99 |
| 2 Jan 1999 | SA 406/8 & 226/7 v WI 212 & 2714th Test · Test | WI | 4 & 33 | - | 2 | South Africa won by 149 runs | Cape Town | West Indies tour of South Africa 1998/99 |
| 26 Dec 1998 | SA 312 & 147/1 v WI 198 & 2593rd Test · Test | WI | 51 & 79 | - | 0 | South Africa won by 9 wickets | Durban | West Indies tour of South Africa 1998/99 |
| 10 Dec 1998 | SA 245 & 195 v WI 121 & 1412nd Test · Test | WI | 4 & 39 | - | 0 | South Africa won by 178 runs | Port Elizabeth | West Indies tour of South Africa 1998/99 |
| 26 Nov 1998 | SA 268 & 164/6 v WI 261 & 1701st Test · Test | WI | 11 & 7 | - | 1 | South Africa won by 4 wickets | Johannesburg | West Indies tour of South Africa 1998/99 |
| 1 Nov 1998 | SA 248/6 v WI 245Final · ODI | WI | 11 | - | 0 | South Africa won by 4 wickets (with 18 balls remaining) | Dhaka | 1998 ICC KnockOut Trophy |
| 31 Oct 1998 | IND 242/6 v WI 245/42nd Semi-Final · ODI | WI | 60* | - | 0 | West Indies won by 6 wickets (with 18 balls remaining) | Dhaka | 1998 ICC KnockOut Trophy |
| 29 Oct 1998 | PAK 259/9 v WI 289/94th QF · ODI | WI | 16 | - | 0 | West Indies won by 30 runs | Dhaka | 1998 ICC KnockOut Trophy |
| 8 Apr 1998 | WI 302/5 v ENG 2455th ODI · ODI | WI | 93 | 0/12 | 0 | West Indies won by 57 runs | Port of Spain | England tour of West Indies 1997/98 |
| 5 Apr 1998 | WI 150/6 v ENG 1494th ODI · ODI | WI | 51 | - | 1 | West Indies won by 4 wickets (with 74 balls remaining) | Kingstown | England tour of West Indies 1997/98 |
| 4 Apr 1998 | WI 213/5 v ENG 209/83rd ODI · ODI | WI | 21 | - | 0 | West Indies won by 5 wickets (with 11 balls remaining) | Kingstown | England tour of West Indies 1997/98 |
| 1 Apr 1998 | WI 267/9 v ENG 2662nd ODI · ODI | WI | 24 | - | 1 | West Indies won by 1 wicket (with 1 ball remaining) | Bridgetown | England tour of West Indies 1997/98 |
| 29 Mar 1998 | WI 277 v ENG 293/51st ODI · ODI | WI | 110 | - | 0 | England won by 16 runs | Bridgetown | England tour of West Indies 1997/98 |
| 20 Mar 1998 | WI 500/7 v ENG 127 & 3216th Test · Test | WI | 89 | - | 2 | West Indies won by an innings and 52 runs | St John's | England tour of West Indies 1997/98 |
| 12 Mar 1998 | WI 262 & 112/2 v ENG 403 & 233/35th Test · Test | WI | 31 & 13* | - | 3 | Match drawn | Bridgetown | England tour of West Indies 1997/98 |
| 27 Feb 1998 | WI 352 & 197 v ENG 170 & 1374th Test · Test | WI | 93 & 30 | - | 4 | West Indies won by 242 runs | Georgetown | England tour of West Indies 1997/98 |
| 13 Feb 1998 | WI 159 & 210 v ENG 145 & 225/73rd Test · Test | WI | 42 & 47 | - | 0 | England won by 3 wickets | Port of Spain | England tour of West Indies 1997/98 |
| 5 Feb 1998 | WI 191 & 282/7 v ENG 214 & 2582nd Test · Test | WI | 55 & 17 | - | 4 | West Indies won by 3 wickets | Port of Spain | England tour of West Indies 1997/98 |
| 19 Dec 1997 | ENG 239/7 v WI 235/7Final · ODI | WI | 2 | - | 0 | England won by 3 wickets (with 11 balls remaining) | Sharjah | 1997–98 Singer Akai Champions Trophy |
