| 01 | Caleb GartnerClass 2021 | 2021 | 16:22.00 | 16:02.84 | RL, St. George's, Nobles at Middlesex · Oct 26, 2019 |
| 02 | Justin O'TooleClass 2020 | 2020 | 16:48.00 | 16:28.33 | RL, St. George's, Nobles at Middlesex · Oct 26, 2019 |
| 03 | Cooper AustenClass 2022 | 2022 | 16:48.00 | 16:28.33 | RL, St. George's, Nobles at Middlesex · Oct 26, 2019 |
| 04 | Mac HaddenClass 2021 | 2021 | 17:13.00 | 16:52.84 | RL, St. George's, Nobles at Middlesex · Oct 26, 2019 |
| 05 | Matt WingClass 2023 | 2023 | 17:28.00 | 17:07.55 | RL, St. George's, Nobles at Middlesex · Oct 26, 2019 |
| 06 | Andrew HarrisClass 2021 | 2021 | 17:28.00 | 17:07.55 | RL, St. George's, Nobles at Middlesex · Oct 26, 2019 |
| 07 | David LathamClass 2021 | 2021 | 17:03.00 | 17:14.19 | NEPSTAs · Nov 9, 2019 |
| 08 | Jack StarobinClass 2020 | 2020 | 18:19.00 | 17:57.55 | RL, St. George's, Nobles at Middlesex · Oct 26, 2019 |
| 09 | Connor CrossClass 2021 | 2021 | 18:38.00 | 18:09.02 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 10 | Cannon CasparClass 2021 | 2021 | 18:47.00 | 18:17.78 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 11 | Peter FaveroClass 2023 | 2023 | 19:17.00 | 18:47.00 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 12 | Caleb KruegerClass 2021 | 2021 | 19:19.00 | 18:48.95 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 13 | Zan DanoffClass 2021 | 2021 | 18:39.00 | 18:51.81 | Groton vs. Middlesex Boys · Oct 11, 2019 |
| 14 | Gavin CassidyClass 2021 | 2021 | 20:23.00 | 19:59.13 | Brooks at Middlesex · Sep 21, 2019 |
| 15 | Stone ShenClass 2022 | 2022 | 20:48.00 | 20:15.65 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 16 | Sean MclaughlinClass 2021 | 2021 | 20:55.00 | 20:22.46 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 17 | Henry HorvathClass 2023 | 2023 | 20:49.00 | 20:24.63 | Lawrence at Middlesex · Sep 14, 2019 |
| 18 | Adam EwingClass 2022 | 2022 | 20:22.00 | 20:35.99 | Groton vs. Middlesex Boys · Oct 11, 2019 |
| 19 | Vedant DeokarClass 2023 | 2023 | 22:23.00 | 21:48.18 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 20 | Sebastian CanizaresClass 2021 | 2021 | 22:03.00 | 22:18.14 | Groton vs. Middlesex Boys · Oct 11, 2019 |
| 21 | Ben LuoClass 2023 | 2023 | 22:55.00 | 22:19.35 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 22 | Richard (yunqi) LiClass 2021 | 2021 | 22:56.00 | 22:20.33 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 23 | Michael ChengClass 2022 | 2022 | 23:00.00 | 22:24.22 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 24 | Raymond LiClass 2023 | 2023 | 22:16.00 | 22:31.29 | Groton vs. Middlesex Boys · Oct 11, 2019 |
| 25 | Hyuntae ChoiClass 2020 | 2020 | 23:17.00 | 22:40.78 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 26 | Justin LiClass 2023 | 2023 | 24:11.00 | 23:33.38 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 27 | Otis HutchesonClass 2021 | 2021 | 24:25.00 | 23:56.41 | Lawrence at Middlesex · Sep 14, 2019 |
| 28 | Julian DaiClass 2022 | 2022 | 24:36.00 | 23:57.73 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 29 | Tim CassidyClass 2023 | 2023 | 24:54.00 | 24:15.27 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 30 | Ethan ChangClass 2022 | 2022 | 24:27.00 | 24:43.79 | Groton vs. Middlesex Boys · Oct 11, 2019 |
| 31 | Cole Jv StewartClass 2023 | 2023 | 26:09.00 | 25:28.32 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 32 | Xander StarobinClass 2023 | 2023 | 26:37.00 | 25:55.60 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 33 | Oliver MitchellClass 2022 | 2022 | 25:38.00 | 25:55.60 | Groton vs. Middlesex Boys · Oct 11, 2019 |
| 34 | Ty WilschutClass 2021 | 2021 | 26:45.00 | 26:03.39 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 35 | Greg Jv LintonClass 2023 | 2023 | 26:52.00 | 26:10.21 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 36 | Andy ChefetzClass 2023 | 2023 | 27:01.00 | 26:18.98 | Middlesex, Sebs, Tabor at Govs · Oct 5, 2019 |
| 37 | Andrew CaoClass 2023 | 2023 | 27:36.00 | 27:03.68 | Lawrence at Middlesex · Sep 14, 2019 |
