2023 CONCACAF Gold Cup Group A

Group A of the 2023 CONCACAF Gold Cup consisted of co-host nation the United States, Jamaica, Trinidad and Tobago and Saint Kitts and Nevis. Nicaragua originally qualified as winners of CONCACAF Nations League B Group C, but were disqualified for fielding ineligible players. They were replaced by Trinidad and Tobago, the runners-up in Group C who had originally qualified for the preliminary round. The group stage was divided between four groups who played from June 24 to July 2, 2023. The top two teams advanced to the quarter-finals, while the other two teams were eliminated.

Standings
In the quarter-finals:
 * The winners of Group A, United States, advanced to play the runners-up of Group D.
 * The runners-up of Group A, Jamaica, advanced to play the winners of Group D.

United States vs Jamaica
The two teams had met 31 times previously, seven of them in the Gold Cup, including the final won 2–1 by the United States in 2017.

Trinidad and Tobago vs Saint Kitts and Nevis
The match marked Saint Kitts and Nevis' debut at the Gold Cup. The two teams had met in 13 previous matches, with 12 victories for Trinidad and Tobago and only one for Saint Kitts and Nevis.

Jamaica vs Trinidad and Tobago
The two teams had faced each other 62 times previously, but never in the Gold Cup. Their most recent meetings were a series of two friendlies played in March 2023, with Trinidad and Tobago winning 1–0 and the sides played to a scoreless draw.

Saint Kitts and Nevis vs United States
Although both are CONCACAF members, the two teams had never met before.

United States vs Trinidad and Tobago
The two teams had faced each other in 27 previous matches including four times in the Gold Cup group stage, all won by the United States (2–1 in the Gold Cup's inaugural edition in 1991, 3–2 in 1996, 2–0 in 2007 and 6–0 in 2019).

Jamaica vs Saint Kitts and Nevis
The two teams had met 10 times previously, most recently in a friendly game in 2018, won 3–1 by Jamaica. This was the first ever Gold Cup match between the two sides as Saint Kitts and Nevis made its debut in the tournament.