Draw: 2021 Gold Cup playoffs

Round 1 (March 2020)
Guadeloupe vs. Saint Vincent and the Grenadines
Barbados vs. Guyana
Bahamas vs. French Guiana
Guatemala vs. Monserrat
Note: Nations League B runners-up vs. League C winners

Round 2 (June 2020)
Haiti vs. Guadeloupe vs. St. Vincent & Gren. winner
Trinidad & Tobago vs. Bahamas/French Guiana winner
Bermuda vs. Bahamas/French Guiana winner
Cuba vs. Guatemala/Monserrat winner
Note: Nations League A third-place teams vs. Round 1 winners
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