Jamaica v Windward Islands Men's First-Class Records
| Number of Matches | 53 | From: 25 January 1969 | To: 07 February 2024 | |
| Jamaica won | 26 | |||
| Windward Islands won | 13 | |||
| Draws | 14 | |||
| Ties | 0 | |||
| 1 match between these teams was abandoned | ||||
Jamaica
| Highest Team Total | 505 for 5 declared | Sabina Park, Kingston | 1987/88 | |
| Lowest All-Out Team Total | 56 | Arnos Vale Playing Field, Kingstown | 2016/17 | |
| Most Runs in innings | 165 | CH Gayle | Sabina Park, Kingston | 2011/12 |
| Best Bowling in innings | 8-47 | DK Jacobs | Beausejour Stadium, Gros Islet | 2013/14 |
| Best Bowling in match | 13-114 | NO Miller | Sabina Park, Kingston | 2017/18 |
| 1st Wkt | 176* | CD Wright (95*) RG Samuels (72*) | Windsor Park, Roseau | 1997/98 |
| 2nd Wkt | 179 | NE Bonner (88) J Blackwood (94) | Beausejour Stadium, Gros Islet | 2013/14 |
| 3rd Wkt | 156 | PJL Dujon (108) MC Neita (58) | Sabina Park, Kingston | 1987/88 |
| 4th Wkt | 162 | NE Bonner (135) P Palmer (114*) | Queen's Park (New), St George's | 2019/20 |
| 5th Wkt | 203 | MN Samuels (160) CS Baugh (92) | Alpart Sports Club, Nain | 2004/05 |
| 6th Wkt | 178 | P Palmer (82) DC Thomas (122) | Arnos Vale Playing Field, Kingstown | 2015/16 |
| 7th Wkt | 134 | RG Samuels (57) NO Perry (76) | Sabina Park, Kingston | 2002/03 |
| 8th Wkt | 76 | NO Miller (39) DK Jacobs (40) | Sabina Park, Kingston | 2015/16 |
| 9th Wkt | 141 | FA Allen (105*) NO Miller (52) | Sabina Park, Kingston | 2017/18 |
| 10th Wkt | 36 | AB Fudadin (81) RH Leveridge (2*) | Sabina Park, Kingston | 2018/19 |
| Note: | A total of 176 was added for the 1st wicket | |||
| 145* | WW Lewis (132) DS Morgan (101*) | Sabina Park, Kingston | 1987/88 | |
| 31 | WW Lewis (132) G Powell (8) | Sabina Park, Kingston | 1987/88 | |
| Most Runs | ||||||||
| Name | Matches | Innings | Not Outs | Runs | HS | Average | ||
| JD Campbell | 14 | 27 | 2 | 839 | 135 | 33.56 |
| Most Wickets | |||||||
| Name | Matches | Balls | Maidens | Runs | Wickets | Average | BB |
| NO Miller | 18 | 5021 | 256 | 1526 | 107 | 14.26 | 8/54 |
| Most Catches | ||
| Name | Matches | Catches |
| CS Baugh | 15 | 23 |
| PJL Dujon | 8 | 23 |
| Most Stumpings | ||
| Name | Matches | Stumpings |
| CS Baugh | 15 | 7 |
Windward Islands
| Highest Team Total | 441 | Sabina Park, Kingston | 1982/83 | |
| Lowest All-Out Team Total | 55 | Alpart Sports Club, Nain | 1998/99 | |
| Most Runs in innings | 154 | DS Smith | Daren Sammy National Cricket Stadium, Gros Islet | 2017/18 |
| Best Bowling in innings | 7-58 | CA Davis | Kaiser Sports Club, Discovery Bay | 1996/97 |
| 7-58 | LAS Sebastien | Sabina Park, Kingston | 2015/16 | |
| Best Bowling in match | 11-93 | ABW Bobb | Sabina Park, Kingston | 2014/15 |
| 1st Wkt | 155 | DS Smith (111) T Theophile (59) | Beausejour Stadium, Gros Islet | 2013/14 |
| 2nd Wkt | 132 | DS Smith (126) J Robinson (64) | Arnos Vale Playing Field, Kingstown | 2015/16 |
| 3rd Wkt | 171 | KAR Hodge (82) AS Athanaze (97) | Guyana National Stadium, Providence | 2022/23 |
| 4th Wkt | 146 | SW Julien (85) JD Charles (73) | Sabina Park, Kingston | 1986/87 |
| 5th Wkt | 110 | DA Joseph (109) DJ Collymore (44) | Sabina Park, Kingston | 1987/88 |
| 6th Wkt | 90 | EWJA Stewart (50) KJ Cottoy (47) | Sabina Park, Kingston | 2019/20 |
| 7th Wkt | 118 | SK Springer (71) RD John (57) | Sabina Park, Kingston | 2023/24 |
| 8th Wkt | 91 | BM Watt (86*) V Dumas (31) | Windsor Park, Roseau | 1997/98 |
| 9th Wkt | 70 | SJ Hinds (72) TZ Kentish (29*) | Sabina Park, Kingston | 1984/85 |
| 10th Wkt | 47 | S Shillingford (19) NT Pascal (28*) | Sabina Park, Kingston | 2011/12 |
| Most Runs | ||||||||
| Name | Matches | Innings | Not Outs | Runs | HS | Average | ||
| DS Smith | 30 | 57 | 6 | 2392 | 154 | 46.90 |
| Most Wickets | |||||||
| Name | Matches | Balls | Maidens | Runs | Wickets | Average | BB |
| S Shillingford | 19 | 4369 | 118 | 2022 | 96 | 21.06 | 7/66 |
| Most Catches | ||
| Name | Matches | Catches |
| DS Smith | 30 | 37 |
| Most Stumpings | ||
| Name | Matches | Stumpings |
| JR Murray | 17 | 5 |
Kevin Jones, Keith Walmsley
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