| 01 | Theodore ChoeClass 2026 | 2026 | 17:35.00 | 17:16.32 | Milton, Nobles, Tabor at St. George's · Oct 11, 2025 |
| 02 | Alex SignorovitchClass 2029 | 2029 | 17:50.00 | 17:20.24 | NEPSTAs · Nov 8, 2025 |
| 03 | Griffin KelleherClass 2027 | 2027 | 17:58.00 | 17:28.02 | NEPSTAs · Nov 8, 2025 |
| 04 | Haotong XueClass 2026 | 2026 | 17:27.00 | 17:33.69 | Milton vs. BB&N boys · Oct 25, 2025 |
| 05 | Jace LivigniClass 2027 | 2027 | 17:47.00 | 17:53.82 | Milton vs. BB&N boys · Oct 25, 2025 |
| 06 | Grant WheelanClass 2029 | 2029 | 17:59.00 | 18:05.90 | Milton vs. BB&N boys · Oct 25, 2025 |
| 07 | Emmett BurghardtClass 2027 | 2027 | 18:29.00 | 18:09.36 | Milton, Nobles, Tabor at St. George's · Oct 11, 2025 |
| 08 | Emlyn JosephClass 2027 | 2027 | 18:16.00 | 18:23.00 | Milton vs. BB&N boys · Oct 25, 2025 |
| 09 | Will FrazierClass 2028 | 2028 | 18:17.00 | 18:24.01 | Milton vs. BB&N boys · Oct 25, 2025 |
| 10 | Alex ShermanClass 2027 | 2027 | 19:07.00 | 18:46.69 | Milton, Nobles, Tabor at St. George's · Oct 11, 2025 |
| 11 | Armand MatijasevicClass 2028 | 2028 | 18:58.00 | 19:05.27 | Milton vs. BB&N boys · Oct 25, 2025 |
| 12 | Hudson LiClass 2026 | 2026 | 19:32.00 | 19:39.49 | Milton vs. BB&N boys · Oct 25, 2025 |
| 13 | Theo EdgarClass 2028 | 2028 | 19:46.00 | 19:53.58 | Milton vs. BB&N boys · Oct 25, 2025 |
| 14 | Hunter CaggianoClass 2027 | 2027 | 20:01.00 | 20:08.67 | Milton vs. BB&N boys · Oct 25, 2025 |
| 15 | Hudson TulmanClass 2029 | 2029 | 20:22.00 | 20:29.81 | Milton vs. BB&N boys · Oct 25, 2025 |
| 16 | Jack ButterworthClass 2026 | 2026 | 20:24.00 | 20:31.82 | Milton vs. BB&N boys · Oct 25, 2025 |
| 17 | William NassClass 2026 | 2026 | 20:39.00 | 20:46.92 | Milton vs. BB&N boys · Oct 25, 2025 |
| 18 | Eli BerkClass 2026 | 2026 | 20:45.00 | 20:52.96 | Milton vs. BB&N boys · Oct 25, 2025 |
| 19 | Owen ChrisensenClass 2029 | 2029 | 20:50.00 | 20:57.99 | Milton vs. BB&N boys · Oct 25, 2025 |
| 20 | Joe JiaClass 2027 | 2027 | 20:54.00 | 21:02.01 | Milton vs. BB&N boys · Oct 25, 2025 |
| 21 | Felix StuartClass 2027 | 2027 | 21:03.00 | 21:11.07 | Milton vs. BB&N boys · Oct 25, 2025 |
| 22 | Mardy Beaumont-MGraduation year unknown | — | 21:27.00 | 21:35.22 | Brooks, Governor's , Lawrence vs. Milton · Sep 27, 2025 |
| 23 | Zifu SongClass 2027 | 2027 | 21:31.00 | 21:39.25 | Milton vs. BB&N boys · Oct 25, 2025 |
| 24 | Daniyal MianClass 2028 | 2028 | 21:36.00 | 21:44.28 | Milton vs. BB&N boys · Oct 25, 2025 |
| 25 | Michael RosaClass 2028 | 2028 | 21:44.00 | 21:52.33 | Milton vs. BB&N boys · Oct 25, 2025 |
| 26 | Alex Landis-ArnoldClass 2026 | 2026 | 22:10.00 | 22:18.50 | Milton vs. BB&N boys · Oct 25, 2025 |
| 27 | Ryan XuClass 2029 | 2029 | 23:16.00 | 23:24.92 | Milton vs. BB&N boys · Oct 25, 2025 |
| 28 | Henry LinClass 2028 | 2028 | 23:18.00 | 23:26.93 | Milton vs. BB&N boys · Oct 25, 2025 |
| 29 | J. JingGraduation year unknown | — | 21:13.00 | 20:50.46 | Milton, Nobles, Tabor at St. George's · Oct 11, 2025 |
| 30 | H. LucianoGraduation year unknown | — | 21:28.00 | 21:36.23 | Brooks, Governor's , Lawrence vs. Milton · Sep 27, 2025 |
| 31 | Arsen ShymonClass 2027 | 2027 | 22:36.30 | 23:10.30 | ISLs · Oct 31, 2025 |
| 32 | O. WongGraduation year unknown | — | 23:59.00 | 24:08.20 | Brooks, Governor's , Lawrence vs. Milton · Sep 27, 2025 |
