2nd Semi-Final, Port of Spain, November 29, 2019, 11:00 PM
268/8(50.0ov)
269/6(49.3ov)
Leeward Islands beat Trinidad and Tobago by 4 wickets
Trinidad and Tobago Playing XI| Darren Bravo | Batsman |
| Yannick Ottley | All Rounder |
| Jason Mohammed | Batsman |
| Anderson Phillip | Bowler |
| Imran Khan (c) | Bowler |
| Akeal Hosein | Bowler |
| Steven Katwaroo † | Wicket Keeper |
| Jeremy Solozano | Batsman |
| Jon-Russ Jaggesar | Bowler |
| Tion Webster | Batsman |
| Keagan Simmons | Batsman |
Leeward Islands Playing XI| Devon Thomas † | Wicket Keeper |
| Kieran Powell | Batsman |
| Jahmar Hamilton (c)† | Wicket Keeper |
| Quinton Boatswain | Bowler |
| Montcin Hodge | Batsman |
| Akeem Saunders | Batsman |
| Jason Campbell | Bowler |
| Amir Jangoo † | Wicket Keeper |
| Keacy Carty | Batsman |
| Terrence Warde | All Rounder |
| Sheeno Berridge | Bowler |