| 01 | Alex TobiasClass 2022 | 2022 | 18:03.00 | 17:52.84 | ISLs · Nov 1, 2019 |
| 02 | Nate WirthClass 2021 | 2021 | 19:54.00 | 19:27.52 | Groton, St. Paul's at Brooks · Sep 14, 2019 |
| 03 | Luke DesmaisonClass 2022 | 2022 | 18:28.00 | 19:55.50 | NEPSTAs · Nov 9, 2019 |
| 04 | NashGraduation year unknown | — | 20:28.00 | 20:00.77 | Brooks vs St. George's, Thayer, St. Sebastian's · Oct 19, 2019 |
| 05 | Nashr El AuliyaClass 2020 | 2020 | 20:00.00 | 20:09.20 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 06 | Jamie LymanClass 2022 | 2022 | 20:45.00 | 20:17.39 | Brooks vs St. George's, Thayer, St. Sebastian's · Oct 19, 2019 |
| 07 | Evan SalhanickClass 2023 | 2023 | 20:46.00 | 20:18.37 | Brooks vs St. George's, Thayer, St. Sebastian's · Oct 19, 2019 |
| 08 | Gardner BrownClass 2021 | 2021 | 20:30.00 | 20:18.46 | ISLs · Nov 1, 2019 |
| 09 | Tanay KommareddiClass 2021 | 2021 | 20:52.00 | 20:40.25 | ISLs · Nov 1, 2019 |
| 10 | Minho EuneClass 2021 | 2021 | 20:54.00 | 21:03.61 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 11 | Adam JacClass 2022 | 2022 | 20:37.00 | 21:39.21 | BB&N Cross Country vs. St. Mark's, Nobles, Brooks · Oct 5, 2019 |
| 12 | Gabriel YuClass 2022 | 2022 | 22:25.00 | 21:55.17 | Brooks vs St. George's, Thayer, St. Sebastian's · Oct 19, 2019 |
| 13 | Gabriel Barreto-D'SilvaClass 2020 | 2020 | 21:18.00 | 22:22.27 | BB&N Cross Country vs. St. Mark's, Nobles, Brooks · Oct 5, 2019 |
| 14 | Daniel ParkClass 2023 | 2023 | 24:08.00 | 23:41.54 | Brooks at Middlesex · Sep 21, 2019 |
| 15 | Edo SpadacciniClass 2022 | 2022 | 24:56.00 | 24:22.82 | Brooks vs St. George's, Thayer, St. Sebastian's · Oct 19, 2019 |
| 16 | Joe ZhaoClass 2022 | 2022 | 26:20.00 | 25:51.13 | Brooks at Middlesex · Sep 21, 2019 |
| 17 | Nick CraryClass 2020 | 2020 | 25:52.00 | 26:03.90 | Brooks vs. Belmont Hill vs. Tabor vs. Milton boys cross-country at Milton · Oct 26, 2019 |
| 18 | Hugh ParkClass 2022 | 2022 | 27:06.00 | 26:29.94 | Groton, St. Paul's at Brooks · Sep 14, 2019 |
| 19 | Sam KimClass 2020 | 2020 | 29:48.00 | 29:15.33 | Brooks at Middlesex · Sep 21, 2019 |
| 20 | Oliver KimClass 2022 | 2022 | 29:55.00 | 29:22.20 | Brooks at Middlesex · Sep 21, 2019 |
| 21 | Tri NguyenClass 2022 | 2022 | 35:26.00 | 34:47.15 | Brooks at Middlesex · Sep 21, 2019 |
| 22 | Adam JinClass 2023 | 2023 | 35:28.00 | 34:49.11 | Brooks at Middlesex · Sep 21, 2019 |
| 23 | Tabor WilsonClass 2022 | 2022 | 20:26.00 | 22:12.88 | NEPSTAs · Nov 9, 2019 |
| 24 | Daniel ReyesClass 2023 | 2023 | 23:18.00 | 24:28.31 | BB&N Cross Country vs. St. Mark's, Nobles, Brooks · Oct 5, 2019 |
| 25 | Ricky BansalClass 2022 | 2022 | 26:41.00 | 28:01.52 | BB&N Cross Country vs. St. Mark's, Nobles, Brooks · Oct 5, 2019 |
| 26 | Shankar ChennattuClass 2022 | 2022 | 29:27.00 | 29:10.42 | ISLs · Nov 1, 2019 |
