On 15 June 2020, CWI held a players' draft for the 2020–21 tournament.[4][5] The draft took place across two rounds,[6][7] with each team signing a minimum of fifteen players.[8][9] In December 2020, Cricket West Indies confirmed that the United States, Canada, Combined Campuses and Colleges and the West Indies Emerging Team would not be taking part in the tournament.[10] On 25 January 2021, CWI announced the schedule for the tournament,[11] with all the squads confirmed two days later.[12]
Following the conclusion of the group stage, Guyana, Jamaica, Trinidad and Tobago and the Windward Islands had all qualified for the semi-finals, with Barbados and the Leeward Islands facing each other in the fifth-place play-off match.[13] In the first semi-final, Trinidad and Tobago beat Jamaica by six wickets to advance to the final.[14] The second semi-final saw Guyana beat the Windward Islands by 95 runs to join Trinidad and Tobago in the final.[15] Trinidad and Tobago won the tournament, beating Guyana by 152 runs in the final.[16]