| 01 | Alex SignorovitchClass 2029 | 2029 | 17:00.00 | 17:07.82 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 02 | Griffin KelleherClass 2027 | 2027 | 17:14.00 | 17:21.92 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 03 | Grant WheelanClass 2029 | 2029 | 17:59.00 | 18:07.27 | Milton vs. BB&N boys · Oct 25, 2025 |
| 04 | Jace LivingiClass 2027 | 2027 | 18:08.00 | 18:16.34 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 05 | Alex ShermanClass 2027 | 2027 | 19:07.00 | 18:48.12 | Milton, Nobles, Tabor at St. George's · Oct 11, 2025 |
| 06 | A. HamodaGraduation year unknown | — | 18:52.00 | 19:00.68 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 07 | H. WetmoreGraduation year unknown | — | 19:01.00 | 19:09.74 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 08 | Will FrazierClass 2028 | 2028 | 19:05.00 | 19:13.78 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 09 | J. McneilGraduation year unknown | — | 19:12.00 | 19:20.83 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 10 | Armand MatijasevicClass 2028 | 2028 | 19:31.00 | 19:39.97 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 11 | Emlyn JosephClass 2027 | 2027 | 19:43.00 | 19:52.07 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 12 | Theo EdgarClass 2028 | 2028 | 19:46.00 | 19:55.09 | Milton vs. BB&N boys · Oct 25, 2025 |
| 13 | Emmett BurghardtClass 2027 | 2027 | 19:51.00 | 20:00.13 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 14 | Hunter CaggianoClass 2027 | 2027 | 20:01.00 | 20:10.20 | Milton vs. BB&N boys · Oct 25, 2025 |
| 15 | Hudson TulmanClass 2029 | 2029 | 20:22.00 | 20:31.37 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 16 | Owen ChrisensenClass 2029 | 2029 | 20:50.00 | 20:59.58 | Milton vs. BB&N boys · Oct 25, 2025 |
| 17 | Joe JiaClass 2027 | 2027 | 20:54.00 | 21:03.61 | Milton vs. BB&N boys · Oct 25, 2025 |
| 18 | Felix StuartClass 2027 | 2027 | 21:11.00 | 21:20.74 | Middlesex, St. Mark's, Sebs at Milton · Sep 19, 2026 |
| 19 | Zifu SongClass 2027 | 2027 | 21:31.00 | 21:40.89 | Milton vs. BB&N boys · Oct 25, 2025 |
| 20 | Daniyal MianClass 2028 | 2028 | 21:36.00 | 21:45.93 | Milton vs. BB&N boys · Oct 25, 2025 |
| 21 | Michael RosaClass 2028 | 2028 | 21:44.00 | 21:53.99 | Milton vs. BB&N boys · Oct 25, 2025 |
| 22 | Ryan XuClass 2029 | 2029 | 23:16.00 | 23:26.70 | Milton vs. BB&N boys · Oct 25, 2025 |
| 23 | Henry LinClass 2028 | 2028 | 23:18.00 | 23:28.71 | Milton vs. BB&N boys · Oct 25, 2025 |
| 24 | Alex NingClass 2027 | 2027 | 19:09.60 | 19:39.91 | ISLs · Nov 3, 2023 |
| 25 | Ernesto OrtizClass 2027 | 2027 | 19:51.00 | 20:53.41 | NEPSTAs · Nov 11, 2023 |
| 26 | True BraunClass 2028 | 2028 | 20:02.00 | 20:11.21 | Tabor at Milton · Oct 14, 2023 |
| 27 | Isaac WuClass 2028 | 2028 | 20:25.23 | 20:57.53 | ISLs · Nov 1, 2024 |
| 28 | Anthony WuClass 2027 | 2027 | 20:31.80 | 21:04.27 | ISLs · Nov 3, 2023 |
| 29 | Jason WuClass 2028 | 2028 | 20:33.00 | 20:42.45 | BH, Nobles, Thayer at Milton · Oct 7, 2023 |
| 30 | Ezra ChenClass 2027 | 2027 | 20:44.50 | 21:17.31 | ISLs · Nov 3, 2023 |
| 31 | G LeeClass 2028 | 2028 | 21:17.00 | 20:48.68 | Middlesex, Milton, Rivers at Brooks · Oct 21, 2023 |
| 32 | Grant KimClass 2028 | 2028 | 21:30.00 | 21:17.90 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton JV Boys · Oct 26, 2024 |
| 33 | Jeff SongClass 2027 | 2027 | 21:46.40 | 22:20.84 | ISLs · Nov 3, 2023 |
| 34 | Leo WanClass 2028 | 2028 | 22:21.00 | 22:08.42 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton JV Boys · Oct 26, 2024 |
| 35 | Gordon YuClass 2027 | 2027 | 22:36.20 | 23:11.95 | ISLs · Nov 3, 2023 |
| 36 | Arsen ShymonClass 2027 | 2027 | 22:36.30 | 23:12.06 | ISLs · Oct 31, 2025 |
| 37 | Chris PengClass 2028 | 2028 | 22:52.00 | 22:39.13 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton JV Boys · Oct 26, 2024 |
| 38 | Mike GaoClass 2028 | 2028 | 23:00.00 | 22:47.05 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton JV Boys · Oct 26, 2024 |
| 39 | Wesley XueClass 2028 | 2028 | 23:00.42 | 23:36.81 | ISLs · Nov 1, 2024 |
| 40 | Zarak AhmadClass 2027 | 2027 | 23:36.90 | 24:14.25 | ISLs · Nov 3, 2023 |
| 41 | Edward QiuClass 2028 | 2028 | 25:49.00 | 26:00.87 | BH, Nobles, Thayer at Milton · Oct 7, 2023 |
