On Saturday, September 22, the Middlesex boys' cross country team raced at Belmont Hill against Belmont Hill, Lawrence Academy, and St. Georges.The varsity squad won every race by a substantial margin; even shutting out Lawrence Academy.

The previous course record at Belmont Hill was 17:00, recorded by Belmont Hill runner Ian Meyer. On Saturday, team captain James Randon won the race with a time of 15:56, breaking Meyer's record by over a minute. Garrett O'toole came in second with a time of 16:08. With these times on their first race, James and Garrett reestablished their prominence in the ISL. Peter Howe finished 4th in the race with a time of 17:22 and is on record pace this season, beating runners in this race that he lost to at the ISL championship race last year. Middlesex's freshman runners, Viraj Deokar and Will Fletcher, along with sophomore Lucas Estrada secured a victory for Middlesex in the varsity race.

Because the varsity race contained 10 Middlesex runners as opposed to the normal 7, the JV was weaker. However, JV still managed to secure a victory over St. Georges, despite their loss to Belmont Hill. This race was the first cross country race for many runners on the team, and their times should improve as the season goes on.