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| Venue | Daren Sammy National Cricket Stadium, Gros Islet on 23rd, 24th, 25th, 26th January 2020 (4-day match) (day/night) |
| Balls per over | 6 |
| Toss | Leeward Islands won the toss and decided to field |
| Result | Leeward Islands won by an innings and 165 runs |
| Points | Windward Islands 3.4 (Bowling 3.4); Leeward Islands 22.4 (Batting 4, Bowling 6.4) |
| Umpires | DK Butler, CO Wright |
| Referee | KP Felix |
| Reserve Umpire | R Banwarie |
| Close of play day 1 | No play |
| Close of play day 2 | Windward Islands (1) 93/6 (Smith 37*, Dember 6*; 44 overs) |
| Close of play day 3 | Leeward Islands (1) 234/5 (Jangoo 50*, Peters 39*; 69 overs) |
| Player of the Match | AS Joseph |
| Windward Islands first innings | Runs | Balls | Mins | 4s | 6s | ||
| DS Smith | b Boatswain | 49 | 194 | 277 | 4 | - | |
| D Maloney | b Joseph | 0 | 5 | 3 | - | - | |
| KAR Hodge | c Cornwall b Berridge | 4 | 4 | 8 | 1 | - | |
| KA Edwards | lbw b Berridge | 4 | 22 | 28 | - | - | |
| *SW Ambris | b Joseph | 1 | 4 | 3 | - | - | |
| AS Athanaze | c Powell b Berridge | 23 | 61 | 101 | 3 | - | |
| +EWJA Stewart | b Berridge | 0 | 2 | 2 | - | - | |
| K Dember | c Thomas b Joseph | 12 | 60 | 88 | 2 | - | |
| SH Lewis | b Joseph | 0 | 28 | 30 | - | - | |
| PAS McSween | not out | 12 | 15 | 28 | 3 | - | |
| J Thomas | b Joseph | 15 | 19 | 23 | 2 | - | |
| Extras | (5 b, 5 lb, 2 nb, 6 w) | 18 | |||||
| Total | (all out, 68.4 overs) | 138 | |||||
| Fall of wickets: | |||||||
| 1-1 (Maloney, 0.6 ov), 2-10 (Hodge, 3.2 ov), 3-27 (Edwards, 9.3 ov), 4-28 (Ambris, 10.1 ov), 5-76 (Athanaze, 33.1 ov), 6-76 (Stewart, 33.3 ov), 7-109 (Dember, 54.1 ov), 8-111 (Lewis, 62.3 ov), 9-111 (Smith, 63.3 ov), 10-138 (Thomas, 68.4 ov) | |||||||
| Leeward Islands bowling | Overs | Mdns | Runs | Wkts | Wides | No-Balls | |
| Joseph | 23.4 | 9 | 41 | 5 | 1 | 1 | |
| Berridge | 19 | 9 | 39 | 4 | 4 | - | |
| Boatswain | 12 | 3 | 32 | 1 | 1 | - | |
| Cornwall | 14 | 6 | 16 | 0 | - | 1 | |
| Leeward Islands first innings | Runs | Balls | Mins | 4s | 6s | ||
| MV Hodge | c Maloney b Thomas | 10 | 33 | 54 | - | - | |
| KOA Powell | lbw b McSween | 69 | 119 | 137 | 9 | - | |
| DC Thomas | c Athanaze b Lewis | 23 | 72 | 98 | 3 | - | |
| KU Carty | b McSween | 0 | 7 | 12 | - | - | |
| *+JN Hamilton | c Hodge b Thomas | 11 | 25 | 34 | 1 | - | |
| AA Jangoo | c Athanaze b Lewis | 51 | 83 | 138 | 5 | - | |
| RJ Peters | b Lewis | 57 | 116 | 138 | 4 | - | |
| AS Joseph | not out | 64 | 56 | 83 | 6 | 3 | |
| RRS Cornwall | c Lewis b Hodge | 37 | 24 | 44 | 2 | 3 | |
| QH Boatswain | not out | 0 | 9 | 7 | - | - | |
| S Berridge | did not bat | ||||||
| Extras | (6 b, 6 lb, 14 nb, 6 w) | 32 | |||||
| Total | (8 wickets, declared, 88.2 overs) | 354 | |||||
| Fall of wickets: | |||||||
| 1-57 (Hodge, 13.1 ov), 2-117 (Powell, 34.1 ov), 3-123 (Carty, 36.4 ov), 4-123 (Thomas, 37.2 ov), 5-149 (Hamilton, 43.1 ov), 6-234 (Jangoo, 69.1 ov), 7-283 (Peters, 77.2 ov), 8-341 (Cornwall, 86.2 ov) | |||||||
| Windward Islands bowling | Overs | Mdns | Runs | Wkts | Wides | No-Balls | |
| Lewis | 18 | 0 | 80 | 3 | 1 | 6 | |
| McSween | 17 | 2 | 68 | 2 | - | - | |
| Hodge | 20.2 | 2 | 60 | 1 | - | - | |
| Dember | 15 | 1 | 44 | 0 | - | 1 | |
| Thomas | 17 | 1 | 87 | 2 | 5 | 7 | |
| Athanaze | 1 | 0 | 3 | 0 | - | - | |
| Windward Islands second innings | Runs | Balls | Mins | 4s | 6s | ||
| D Maloney | b Berridge | 4 | 11 | 12 | - | - | |
| KAR Hodge | c Hodge b Berridge | 9 | 77 | 139 | - | - | |
| KA Edwards | c Hamilton b Berridge | 0 | 8 | 10 | - | - | |
| *SW Ambris | b Berridge | 4 | 9 | 11 | 1 | - | |
| AS Athanaze | c Hamilton b Boatswain | 0 | 4 | 4 | - | - | |
| +EWJA Stewart | b Berridge | 11 | 29 | 32 | 2 | - | |
| DS Smith | lbw b Cornwall | 3 | 21 | 21 | - | - | |
| K Dember | run out (Carty) | 1 | 2 | 13 | - | - | |
| SH Lewis | lbw b Cornwall | 0 | 14 | 14 | - | - | |
| PAS McSween | c Powell b Joseph | 0 | 18 | 24 | - | - | |
| J Thomas | not out | 8 | 9 | 15 | 2 | - | |
| Extras | (2 b, 1 lb, 5 nb, 3 w) | 11 | |||||
| Total | (all out, 33 overs) | 51 | |||||
| Fall of wickets: | |||||||
| 1-7 (Maloney, 3.1 ov), 2-7 (Edwards, 5.3 ov), 3-13 (Ambris, 7.6 ov), 4-14 (Athanaze, 8.5 ov), 5-28 (Stewart, 15.6 ov), 6-36 (Smith, 21.6 ov), 7-38 (Dember, 23.6 ov), 8-42 (Lewis, 27.5 ov), 9-43 (Hodge, 29.3 ov), 10-51 (McSween, 33 ov) | |||||||
| Leeward Islands bowling | Overs | Mdns | Runs | Wkts | Wides | No-Balls | |
| Joseph | 9 | 5 | 10 | 1 | - | 1 | |
| Berridge | 10 | 4 | 22 | 5 | 2 | - | |
| Boatswain | 7 | 3 | 9 | 1 | 1 | 1 | |
| Cornwall | 6 | 3 | 7 | 2 | - | 2 | |
| Thomas | 1 | 1 | 0 | 0 | - | - | |
Notes
--> KA Edwards made his last appearance in First-Class matches
--> AS Athanaze (1) passed 500 runs in First-Class matches when he reached 3
--> K Dember (1) equalled his previous highest score of 12 in First-Class matches
--> J Thomas (1) passed his previous highest score of 13 in First-Class matches
--> AS Joseph (1) passed his previous highest score of 47 in First-Class matches
--> S Berridge achieved his best innings bowling analysis in First-Class matches in the Windward Islands second innings (previous best was 5-59)
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