August 19, 2023 0 - 5 Premier League UPSL Fall 2023 N/A Rockville Soccer Club vs Sure Sports FC
August 26, 2023 3 - 0 Premier League UPSL Fall 2023 N/A Home Game Opener
August 26, 2023 3 - 0 Premier League UPSL Fall 2023 N/A Sure Sports FC vs MoCo 1776
September 3, 2023 1 - 1 Premier League UPSL Fall 2023 N/A Maryland Bobcat FC vs Sure Sports FC
September 9, 2023 3 - 2 Premier League UPSL Fall 2023 N/A Sure Sports FC vs Germantown FC
September 16, 2023 5:00 pm Premier League UPSL Fall 2023 N/A Fredericks Skyline Club vs Sure Sports FC
September 23, 2023 5:00 pm Premier League UPSL Fall 2023 N/A Sure Sports FC vs Dream FC
September 30, 2023 4:00 pm Premier League UPSL Fall 2023 N/A Bridge Sports Club vs Sure Sports FC
October 7, 2023 5:00 pm Premier League UPSL Fall 2023 N/A Sure Sports FC vs Athletic United FC
October 17, 2023 TBD Premier League UPSL Fall 2023 N/A Sure Sports FC vs Bridge Sports Club