The qualifying phase of the 2019–20 CONCACAF Nations League was a one-off tournament that took place from 6 September 2018 to 24 March 2019. The qualifying determined the seeding for the group phase of the inaugural tournament, as well as determining the remaining ten teams that qualified for the 2019 CONCACAF Gold Cup.
Apart from the 6 teams which participated in the 2018 FIFA World Cup qualifying hexagonal, the other 34 teams (Guatemala could not enter due to FIFA suspension after missing the deadline of 1 March 2018) entered qualifying. Subsequently, each team played four matches, two home and two away. Based on their results, the teams were divided into tiers for the group phase of the inaugural edition of the CONCACAF Nations League:
The top 6 teams qualified for League A to join the 6 hexagonal participants.
The next 16 teams qualified for League B.
The last 12 teams qualified for League C to join Guatemala.
The 34 teams were seeded into four pots based on their position in the March 2018 CONCACAF Ranking Index (shown in parentheses). Pots A and D contained 8 teams, while pots B and C contained 9 teams.
The order of the match pairings per each FIFA match window was as follows:
6–11 September 2018
Pot A v Pot D, Pot B v Pot C
B2 v C7, A6 v D5, D3 v A8, D8 v A1, C9 v B6, C1 v B8, B3 v C6, A3 v D4, A4 v D6, B9 v C2, D7 v A2, C5 v B4, D2 v A5, A7 v D1, B7 v C8, B1 v C3, C4 v B5
11–16 October 2018
Pot A v Pot C, Pot B v Pot D, 1 team from Pot B v 1 team from Pot C
D6 v B7, A2 v C8, B6 v D1, B4 v D4, C6 v A7, B5 v D8, B8 v D5, C3 v B3, D7 v B1, A5 v C9, C7 v A6, C2 v A4, A8 v C1, D2 v B2, D3 v B9, A1 v C4, C5 v A3
16–20 November 2018
Pot A v Pot B, Pot C v Pot D, 1 team from Pot B v 1 team from Pot C
C2 v D2, D6 v C4, A1 v B7, D5 v C5, B2 v A8, A4 v B4, B5 v A7, C3 v D8, C8 v D3, D1 v C1, B9 v A5, A3 v B8, C9 v D7, D4 v C6, A6 v B3, B6 v A2, B1 v C7
21–24 March 2019
Pot A v Pot A, Pot B v Pot B, Pot C v Pot C, Pot D v Pot D, 1 team from Pot B v 1 team from Pot C
A8 v A1, B3 v B9, B4 v B6, A7 v A4, C8 v B5, D1 v D2, D4 v D7, B8 v B2, C6 v C9, C7 v C2, A5 v A6, C1 v C3, D5 v D6, B7 v B1, A2 v A3, C4 v C5, D8 v D3
The draw of the qualifying fixtures was held on 7 March 2018, 10:00 EST (UTC−5), at The Temple House in Miami Beach, Florida, United States, directly after the launch event of the CONCACAF Nations League. A computerized pre-draw produced a "master schedule", creating 17 fixtures for each matchday. The teams in each pot were then drawn to the corresponding positions in the schedule (A1–A8, B1–B9, C1–C9, D1–D8). The computer model assured that no teams face each other more than once, and that each team plays two home and two away matches.
The match dates were announced on 29 May 2018, with the venues announced in August and September 2018. The March 2019 match schedule was revised by CONCACAF in January 2019.
^ abCONCACAF awarded Guyana a 3–0 win as a result of Barbados fielding the ineligible players Hallam Hope and Krystian Pearce. The Barbados FA had not completed a request with FIFA to change association of the former England youth internationals. The match originally ended 2–2.
^ abDominica played their home match against Suriname in Guadeloupe.
^ abThe U.S. Virgin Islands played their home matches in the United States.
^ abSaint Martin played their home matches in Anguilla.
^The Martinique v British Virgin Islands match, originally scheduled on 11 September 2018, 20:00 EDT, was postponed due to the potential impact of Hurricane Isaac on Martinique. The match was rescheduled to 16 October 2018, 19:00 EDT.
^The Puerto Rico v Martinique match, originally scheduled on 15 October 2018, 16:00 EDT, was rescheduled to 13 October 2018, 16:00 EDT, due to the rescheduling of the Martinique v British Virgin Islands match.
^Sint Maarten played their home matches in Anguilla.
^The British Virgin Islands v Bonaire match, originally scheduled on 16 November 2018, 13:45 EST (14:45 UTC−4), was rescheduled to 24 March 2019, 15:00 EDT, due to canceled flights of the teams.
^ abThe British Virgin Islands played their home matches in Anguilla.
^The British Virgin Islands v Turks and Caicos Islands match, originally scheduled on 21 March 2019, 16:00 EDT, was later moved to 15:00 EDT.
^The Saint Vincent and the Grenadines v Bonaire match, originally scheduled on 22 March 2019, 15:00 EDT, was rescheduled to 21 March 2019, 15:00 EDT, due to the rescheduling of the British Virgin Islands v Bonaire match.
^The Anguilla v U.S. Virgin Islands match, originally scheduled on 22 March 2019, 18:00 EDT, was later moved to 15:00 EDT.
^"CONCACAF Launches New Ranking Index". CONCACAFNationsLeague.com. The Confederation of North, Central American and Caribbean Association Football. 2 March 2018. Archived from the original on 2 September 2018. Retrieved 2 March 2018.