| 01 | Ross TejedaClass 2022 | 2022 | 16:04.70 | 16:28.88 | ISLs · Nov 5, 2021 |
| 02 | Tommy GaffeyClass 2020 | 2020 | 16:43.00 | 16:32.33 | ISLs · Nov 1, 2019 |
| 03 | James PenerClass 2023 | 2023 | 17:03.70 | 17:29.36 | ISLs · Nov 5, 2021 |
| 04 | Charlie GavinClass 2024 | 2024 | 17:32.00 | 17:44.04 | Rivers, Tabor, Thayer at Groton · Oct 28, 2023 |
| 05 | Brendan BrosnanClass 2025 | 2025 | 18:00.00 | 17:48.51 | St. Mark's vs Thayer · Oct 19, 2024 |
| 06 | Ryan ChiariClass 2022 | 2022 | 17:35.70 | 18:02.16 | ISLs · Nov 5, 2021 |
| 07 | Theodore DowdClass 2025 | 2025 | 18:01.00 | 18:14.37 | XC at Tabor · Oct 5, 2024 |
| 08 | Jaden SmithClass 2024 | 2024 | 19:09.00 | 18:20.28 | NEPSTAs · Nov 11, 2023 |
| 09 | Steven SilversClass 2025 | 2025 | 18:41.00 | 18:29.08 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton · Oct 26, 2024 |
| 10 | Garner ThompsonClass 2020 | 2020 | 18:42.00 | 18:30.07 | ISLs · Nov 1, 2019 |
| 11 | Luke DriscollClass 2025 | 2025 | 18:08.60 | 18:35.89 | ISLs · Nov 3, 2023 |
| 12 | Grant ColdrenClass 2021 | 2021 | 18:35.00 | 18:47.76 | Groton vs. BB&N, Governor's, Thayer Varsity Boys · Oct 26, 2019 |
| 13 | Dylan CrawfordClass 2028 | 2028 | 19:00.00 | 18:47.88 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton · Oct 26, 2024 |
| 14 | Owen HaskellClass 2027 | 2027 | 19:18.00 | 18:53.19 | NEPSTAs · Nov 8, 2025 |
| 15 | Calvin JacobsClass 2029 | 2029 | 19:28.00 | 18:57.72 | Thayer at Govs · Oct 17, 2025 |
| 16 | Gabby GuerreroClass 2024 | 2024 | 18:47.00 | 18:59.90 | Groton vs. BB&N, Governor's, Thayer Varsity Boys · Oct 26, 2019 |
| 17 | Aidan HumphriesClass 2022 | 2022 | 18:49.00 | 19:01.92 | Groton vs. BB&N, Governor's, Thayer Varsity Boys · Oct 26, 2019 |
| 18 | Ryan NorekeClass 2024 | 2024 | 19:28.00 | 19:15.58 | Nobles, Sebs, Thayer at St. Mark's · Sep 24, 2022 |
| 19 | Oliver MasseyClass 2028 | 2028 | 19:47.00 | 19:16.23 | Governor's vs. Rivers vs. St. Sebastian's vs. Thayer · Oct 11, 2025 |
| 20 | Robert PeirceClass 2028 | 2028 | 19:42.00 | 19:16.68 | NEPSTAs · Nov 8, 2025 |
| 21 | Tom GaynorClass 2025 | 2025 | 18:49.20 | 19:17.50 | ISLs · Nov 5, 2021 |
| 22 | Seamus McfarlandClass 2028 | 2028 | 18:52.21 | 19:20.59 | ISLs · Oct 31, 2025 |
| 23 | John BriceClass 2025 | 2025 | 20:14.00 | 19:22.53 | NEPSTAs · Nov 11, 2023 |
| 24 | Evan SchneiderClass 2025 | 2025 | 19:51.00 | 19:38.33 | St. Mark's vs Thayer · Oct 19, 2024 |
| 25 | Christian MaccallumClass 2025 | 2025 | 19:38.00 | 19:45.53 | BH, Nobles, Thayer at Milton · Oct 7, 2023 |
| 26 | Quinn BartlingClass 2027 | 2027 | 20:30.00 | 19:58.11 | Thayer at Govs · Oct 17, 2025 |
| 27 | SchaedlerGraduation year unknown | — | 20:11.00 | 19:58.12 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton · Oct 26, 2024 |
| 28 | C. ThompsonGraduation year unknown | — | 20:56.00 | 20:02.75 | Varsity Boys at RL · Oct 5, 2019 |
| 29 | Benjamin KoperClass 2022 | 2022 | 19:54.00 | 20:07.67 | Groton vs. BB&N, Governor's, Thayer Varsity Boys · Oct 26, 2019 |
| 30 | Griffin GibbsClass 2022 | 2022 | 20:02.00 | 20:15.15 | NEPSTAs · Nov 9, 2019 |
| 31 | Jake DevriesClass 2025 | 2025 | 20:00.00 | 20:22.72 | St. Mark's at Thayer · Sep 22, 2023 |
| 32 | Kj IrvingClass 2028 | 2028 | 19:53.52 | 20:23.44 | ISLs · Oct 31, 2025 |
| 33 | Quinlan BartlingClass 2027 | 2027 | 19:54.86 | 20:24.81 | ISLs · Oct 31, 2025 |
| 34 | Brandon AbellClass 2028 | 2028 | 21:06.00 | 20:33.18 | Governor's vs. Rivers vs. St. Sebastian's vs. Thayer · Oct 11, 2025 |
| 35 | Peter ChenClass 2023 | 2023 | 20:21.20 | 20:36.30 | Middlesex, Milton, Thayer at Tabor · Oct 29, 2022 |
| 36 | Conor MannionClass 2023 | 2023 | 20:11.00 | 20:41.35 | ISLs · Nov 5, 2021 |
| 37 | R. ParkerGraduation year unknown | — | 21:22.00 | 20:48.76 | Governor's vs. Rivers vs. St. Sebastian's vs. Thayer · Oct 11, 2025 |
| 38 | Connor KeleherClass 2028 | 2028 | 21:17.00 | 20:52.08 | Milton, Thayer, Belmont at Middlesex · Oct 4, 2025 |
| 39 | Tripp LallyClass 2029 | 2029 | 20:23.95 | 20:54.63 | ISLs · Oct 31, 2025 |
| 40 | Jonah RothmanClass 2022 | 2022 | 20:24.20 | 20:54.89 | ISLs · Nov 5, 2021 |
| 41 | Michael ScullyClass 2025 | 2025 | 21:51.00 | 20:55.41 | BB&N, D-S, Nobles, Sebs, Thayer at Latin · Oct 8, 2021 |
| 42 | Alec BorgesClass 2022 | 2022 | 21:10.00 | 20:56.49 | St. Mark's (SM) vs Middlesex (MX), Milton (MA) & Thayer · Sep 28, 2019 |
| 43 | Eli KreamClass 2023 | 2023 | 21:04.00 | 21:18.47 | Groton vs. BB&N, Governor's, Thayer JV Boys · Oct 26, 2019 |
| 44 | Tommy BiClass 2023 | 2023 | 21:03.00 | 21:26.91 | Rivers at Thayer · Oct 15, 2022 |
| 45 | Thomas CasallClass 2029 | 2029 | 22:27.00 | 21:58.15 | NEPSTAs · Nov 8, 2025 |
| 46 | Sebastian KeleherClass 2024 | 2024 | 23:01.00 | 22:02.45 | NEPSTAs · Nov 11, 2023 |
| 47 | Tony YinClass 2025 | 2025 | 22:22.00 | 22:07.73 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton JV Boys · Oct 26, 2024 |
| 48 | Chris BarrettClass 2022 | 2022 | 21:38.30 | 22:10.84 | ISLs · Nov 5, 2021 |
| 49 | L. TrippGraduation year unknown | — | 22:40.00 | 22:25.54 | September 27 at St. Mark's · Sep 27, 2025 |
| 50 | C. HamiltonGraduation year unknown | — | 23:57.00 | 22:56.07 | Varsity Boys at RL · Oct 5, 2019 |
| 51 | Connor BraggClass 2028 | 2028 | 23:21.00 | 23:06.10 | St. Mark's vs. Belmont Hill vs. Thayer vs. Milton JV Boys · Oct 26, 2024 |
| 52 | Andy LiuClass 2029 | 2029 | 23:44.00 | 23:07.08 | Thayer at Govs · Oct 17, 2025 |
| 53 | Thomas LovellGraduation year unknown | — | 22:44.00 | 23:09.82 | St. Mark's at Thayer · Sep 19, 2025 |
| 54 | Charlie GilmanClass 2025 | 2025 | 24:17.00 | 23:15.22 | NEPSTAs · Nov 11, 2023 |
