2023 CONCACAF Caribbean Cup knockout stage

The 2023 CONCACAF Caribbean Cup knockout stage was played from 24 October to 6 December 2023. A total of 4 teams competed in the knockout stage to decide the champions of the 2023 CONCACAF Caribbean Cup.

Qualified teams
 The winners and runners-up of each of the four groups in the group stage advanced to the quarter-finals.

Format
 The knockout stage was played on a single-elimination tournament with the following rules:
 * Each tie was played on a home-and-away two-legged basis. The home team of the second leg in each tie was determined separately for each round as follows (Regulations Article 12.9):
 * In the semi-finals, the group winners hosted the second leg.
 * In the finals, the higher-ranked team based on total points accumulated in the group stage and semi-finals hosted the second leg.
 * In the semi-finals, if tied on aggregate, the away goals rule would be used. If still tied, the penalty shoot-out would be directly used to determine the winners (Regulations Article 12.8.2).
 * In the third place play-offs and finals, if tied on aggregate, the away goals rule would also be used. If still tied, 30 minutes of extra time would be played but the away goals scored during this time would not serve as a tie-breaking criteria. If still tied after extra time, the penalty shoot-out would be used to determine the winner (Regulations Article 12.8.3).

Bracket
The bracket of the final stages was determined as follows:  The bracket was pre-determined as follows.



Summary
 The first legs were played on 24–25 October, and the second legs were played on 31 October – 2 November 2023.


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Matches
''Cavalier won 5–0 on aggregate, advanced to the finals and qualified for the 2024 CONCACAF Champions Cup Round One at minimum. Harbour View advanced to the third place play-off.''

''Tied 1–1 on aggregate, Robinhood won on penalties, advanced to the finals and qualified for the 2024 CONCACAF Champions Cup Round One at minimum. Moca advanced to the third place play-off.''

Third place play-offs
In the third place play-offs, the team which had the better performances across all previous rounds (group stage and semi-finals) hosted the second leg.

Summary



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Matches
Moca won 3–2 on aggregate and qualified for the 2024 CONCACAF Champions Cup Round One.

Finals
In the finals, the team which had the better performances across all previous rounds (group stage and semi-finals) hosted the second leg.

Summary



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Matches
Robinhood won 3–0 on aggregate and qualified for the 2024 CONCACAF Champions Cup Round of 16.