The Competitions Committee has announced the matchups for the first round of the 2023/24 FA Challenge Cup, presented by Lindo's Group of Companies. These matches will take place between January 18th and 21st, 2024. The dates, time and venues for each matchup are listed below in order of when the game is scheduled to take place.

Boulevard vs St. George's Colts

• Date: Thursday, January 18, 2024
• Kickoff Time: 9:15 PM
• Venue: Goose Gosling (BAA) Field

Devonshire Cougars vs Robin Hood

• Date: Friday, January 19, 2024
• Kickoff Time: 8:00 PM
• Venue: Devonshire Recreation Club

Southampton Rangers vs Pembroke Hamilton Club

• Date: Saturday, January 20, 2024
• Kickoff Time: 2:30 PM
• Venue: Southampton Oval

X-Roads vs Tuff Dogs

• Date: Sunday, January 21, 2024
• Kickoff Time: 12:00 PM
• Venue: St. David's

Devonshire Colts vs St. David's

• Date: Sunday, January 21, 2024
• Kickoff Time: 12:00 PM
• Venue: Police Field

North Village Community Club vs Young Men's Social Club

• Date: Sunday, January 21, 2024
• Kickoff Time: 2:30 PM
• Venue: Bernard's Park

Hamilton Parish Workmen's Club vs Paget FC

• Date: Sunday, January 21, 2024
• Kickoff Time: 2:30 PM
• Venue: Wellinton Oval

Dandy Town vs Somerset Trojans

• Date: Sunday, January 21, 2024
• Kickoff Time: 6:00 PM
• Venue: Goose Gosling (BAA) Field

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For updated information regarding the Senior Men's leagues, click here.