| Sep 19, 2026 | Middlesex, St. Mark's, St. Sebastian's at MiltonSep 19, 2026 · Place 14 | Milton Standard 5K | Raw 19:05.00Adj. 19:13.78 | 14 |
| Nov 8, 2025 | NEPSTA Division I Championship (JV)Nov 8, 2025 · Place 50 | Taft School 5K | Raw 20:11.00Adj. 19:38.81 | 50 |
| Oct 31, 2025 | Independent School League (ISL) Championship (JV)Oct 31, 2025 · Place 7 | Wrentham Championship 5K | Raw 18:18.03Adj. 18:46.98 | 7 |
| Oct 25, 2025 | Milton Academy vs. BB&N boys cross countryOct 25, 2025 · Place 12 | Milton Standard 5K | Raw 18:17.00Adj. 18:25.41 | 12 |
| Oct 18, 2025 | Milton (M) vs. Nobles (N) vs. Middlesex (MX)Oct 18, 2025 · Place 12 | Milton Standard 5K | Raw 18:30.00Adj. 18:38.51 | 12 |
| Oct 11, 2025 | Milton Academy, Nobles, Tabor at St. George'sOct 11, 2025 · Place 22 | St. Georges 5K | Raw 19:02.00Adj. 18:43.20 | 22 |
| Oct 4, 2025 | Middlesex Cross Country hosting Milton, Thayer, BelmontOct 4, 2025 · Place 19 | Middlesex 5K Course | Raw 19:36.00Adj. 19:14.51 | 19 |
| Sep 27, 2025 | Brooks, Governor's Academy, Lawrence Academy vs. Milton AcademySep 27, 2025 · Place 12 | Milton Standard 5K | Raw 19:12.00Adj. 19:20.83 | 12 |
| Nov 9, 2024 | NEPSTA Division I Championship (JV)Nov 9, 2024 · Place 54 | Hotchkiss School 5K | Raw 19:39.00Adj. 19:43.71 | 54 |
| Nov 1, 2024 | Independent School League (ISL) Championship (JV)Nov 1, 2024 · Place 60 | Wrentham Championship 5K | Raw 20:18.29Adj. 20:50.41 | 60 |
| Oct 26, 2024 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton AcademyOct 26, 2024 · Place 24 | St. Mark's School Championship Course | Raw 20:06.00Adj. 19:54.68 | 24 |
| Oct 19, 2024 | Governor's School vs. Milton AcademyOct 19, 2024 · Place 12 | Milton Standard 5K | Raw 19:40.00Adj. 19:49.04 | 12 |
| Oct 11, 2024 | CROSS-COUNTRY AT ROXBURY LATIN SCHOOL (JV)Oct 11, 2024 · Place 8 | RL 5K Course | Raw 21:06.00Adj. 20:13.86 | 8 |
| Oct 5, 2024 | Milton Academy vs Rivers, St. George's, Lawrence Academy (JV)Oct 5, 2024 · Place 20 | Milton Standard 5K | Raw 20:02.00Adj. 20:11.21 | 20 |
| Sep 28, 2024 | Governor's vs. Groton, Milton Academy, Tabor, BrooksSep 28, 2024 · Place 29 | Governor's 5K Course | Raw 21:01.00Adj. 20:29.86 | 29 |
| Sep 21, 2024 | Boys XC at NoblesSep 21, 2024 · Place 30 | Noble and Greenough School 5K | Raw 21:30.00Adj. 20:36.02 | 30 |