| 01 | Aj StrangClass 2022 | 2022 | 16:33.00 | 16:39.35 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 02 | Max LitvakClass 2020 | 2020 | 18:27.00 | 18:07.40 | Boys Combined V & JV · Oct 5, 2019 |
| 03 | Ryan WeiClass 2022 | 2022 | 18:30.00 | 18:20.35 | NEPSTAs · Nov 9, 2019 |
| 04 | Peter LeitzesClass 2024 | 2024 | 18:33.00 | 18:40.11 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 05 | Jehan BoerClass 2021 | 2021 | 19:00.00 | 18:47.88 | ISLs · Nov 1, 2019 |
| 06 | Pedro MateoClass 2021 | 2021 | 18:46.00 | 18:53.20 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 07 | Aston ChanClass 2022 | 2022 | 19:11.00 | 18:58.76 | ISLs · Nov 1, 2019 |
| 08 | Zach NeriClass 2021 | 2021 | 19:25.00 | 19:14.87 | NEPSTAs · Nov 9, 2019 |
| 09 | Jack SullivanClass 2020 | 2020 | 19:33.00 | 19:40.50 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 10 | Christian WestphalClass 2021 | 2021 | 19:35.00 | 19:42.51 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 11 | Tim FanClass 2021 | 2021 | 20:06.00 | 19:44.65 | Boys Combined V & JV · Oct 5, 2019 |
| 12 | Yaman HabipClass 2023 | 2023 | 20:42.00 | 20:20.01 | Boys Combined V & JV · Oct 5, 2019 |
| 13 | Jacob (coby) MullikenClass 2023 | 2023 | 20:45.00 | 20:22.96 | Boys Combined V & JV · Oct 5, 2019 |
| 14 | Seb ParkClass 2021 | 2021 | 21:25.00 | 21:02.25 | Boys Combined V & JV · Oct 5, 2019 |
| 15 | Alex RodriguezClass 2020 | 2020 | 21:30.00 | 21:07.16 | Boys Combined V & JV · Oct 5, 2019 |
| 16 | Zach RahamanClass 2021 | 2021 | 21:46.00 | 21:22.88 | Boys Combined V & JV · Oct 5, 2019 |
| 17 | Margo BeckerClass 2020 | 2020 | 20:25.00 | 21:24.98 | Milton at BB&N · Sep 21, 2019 |
| 18 | Elliot SmithClass 2022 | 2022 | 21:49.00 | 21:25.82 | Boys Combined V & JV · Oct 5, 2019 |
| 19 | Jack BurtonClass 2022 | 2022 | 20:28.00 | 21:28.13 | Milton at BB&N · Sep 21, 2019 |
| 20 | Thomas StrongClass 2023 | 2023 | 20:29.00 | 21:29.18 | Milton at BB&N · Sep 21, 2019 |
| 21 | Evan ZhangClass 2023 | 2023 | 21:58.00 | 21:34.66 | Boys Combined V & JV · Oct 5, 2019 |
| 22 | Victor XuClass 2023 | 2023 | 22:05.00 | 21:41.54 | Boys Combined V & JV · Oct 5, 2019 |
| 23 | Justin LinClass 2020 | 2020 | 22:44.00 | 22:19.85 | Boys Combined V & JV · Oct 5, 2019 |
| 24 | Jack DarlingClass 2021 | 2021 | 21:27.00 | 22:30.02 | Milton at BB&N · Sep 21, 2019 |
| 25 | Teddy SunshineClass 2022 | 2022 | 23:54.00 | 23:28.61 | Boys Combined V & JV · Oct 5, 2019 |
| 26 | Myles NdirituClass 2022 | 2022 | 24:53.00 | 24:26.56 | Boys Combined V & JV · Oct 5, 2019 |
| 27 | Andrew RodriguezClass 2023 | 2023 | 25:31.00 | 25:03.89 | Boys Combined V & JV · Oct 5, 2019 |
| 28 | Ryan ShueClass 2023 | 2023 | 24:13.00 | 25:24.14 | Milton at BB&N · Sep 21, 2019 |
| 29 | Ameen SheikhClass 2022 | 2022 | 24:59.00 | 26:12.40 | Milton at BB&N · Sep 21, 2019 |
| 30 | Desman WardClass 2023 | 2023 | 22:46.00 | 22:54.73 | Brooks vs. Tabor vs. Belmont Hill vs. Milton JV Boys Cross-Country at Milton · Oct 26, 2019 |
| 31 | Yavuz ShazadClass 2022 | 2022 | 23:03.00 | 23:11.84 | Brooks vs. Tabor vs. Belmont Hill vs. Milton JV Boys Cross-Country at Milton · Oct 26, 2019 |
| 32 | Jeremy HwangClass 2022 | 2022 | 23:12.00 | 23:20.90 | Brooks vs. Tabor vs. Belmont Hill vs. Milton JV Boys Cross-Country at Milton · Oct 26, 2019 |
| 33 | Ben SerraClass 2022 | 2022 | 24:23.00 | 24:32.35 | Brooks vs. Tabor vs. Belmont Hill vs. Milton JV Boys Cross-Country at Milton · Oct 26, 2019 |
