| 1 | 8:15.13 | Collin GilstrapStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2025 |
| 2 | 8:23.77 | Luke CoulterRiverhead | Riverhead '16 | Stony Brook Snowflake Classic | 2022 |
| 3 | 8:25.90 | Michael WattsStony Brook | Stony Brook | Stony Brook University Season Opener | 2017 |
| 4 | 8:27.60 | Vann MoffettStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2017 |
| 5 | 8:28.56 | Alex KramerNorthport | Northport '13 | Stony Brook University - Wolfie Invitational | 2014 |
| 6 | 8:30.42 | Cameron AveryStony Brook | Stony Brook | Stony Brook University Season Opener | 2017 |
| 7 | 8:30.51 | Eben BraggStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2022 |
| 8 | 8:31.57 | Eric SpeakmanStony Brook | Stony Brook | Stony Brook University Spring Opener | 2015 |
| 9 | 8:31.60 | Kevin VinolasStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2017 |
| 10 | 8:31.63 | Henry GartnerStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2024 |
| 11 | 8:33.01 | Joseph BertolaStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2025 |
| 12 | 8:33.50 | Greg MangarelliStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2017 |
| 13 | 8:33.72 | Mitchell KunStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2014 |
| 14 | 8:35.45 | Darian SorouriStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2018 |
| 15 | 8:35.65 | Daniel ConnellyMount Sinai | Mount Sinai '14 | Stony Brook University Season Opener | 2017 |
| 16 | 8:38.94 | Finn BurkeStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2024 |
| 17 | 8:47.96 | Daniel DenisStony Brook | Stony Brook | Stony Brook University Spring Opener | 2015 |
| 18 | 8:48.78 | Benjamin McDermotStony Brook | Stony Brook | Stony Brook University Season Opener | 2017 |
| 19 | 8:51.59 | Thomas RammelkampMiller Place | Miller Place '07 | Stony Brook University Track & Field Invitati | 2012 |
| 20 | 8:54.88 | Nick CruzStony Brook | Stony Brook | Stony Brook University Season Opener | 2017 |
| 21 | 8:56.29 | Matt ZamparielloSt. John the Baptist | St. John the Baptist '11 | Stony Brook University - Wolfie Invitational | 2015 |
| 22 | 8:56.30 | Bryce HedmanStony Brook | Stony Brook | Stony Brook University Season Opener | 2017 |
| 23 | 8:56.78 | Ryan ClarkeStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2014 |
| 24 | 8:58.33 | Neel ChitturStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2024 |
| 25 | 8:58.53 | Mason TalaricoStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2024 |
| 26 | 8:58.54 | Mark ValentinoSmithtown West | Smithtown West '11 | Stony Brook University - Wolfie Invitational | 2015 |
| 27 | 9:00.34 | Nicholas LemonStony Brook | Stony Brook | Stony Brook University Track & Field Invitati | 2012 |
| 28 | 9:02.18 | Connor McAlaryShoreham-Wading River | Shoreham-Wading River '14 | Stony Brook University - Wolfie Invitational | 2016 |
| 29 | 9:03.51 | Matthew LeeStony Brook | Stony Brook | Stony Brook University Spring Opener | 2015 |
| 30 | 9:03.94 | William WhelanSachem East | Sachem East '08 | Stony Brook University - Wolfie Invitational | 2018 |
| 31 | 9:07.26 | Victor GarifoBayport-Blue Point | Bayport-Blue Point '16 | Stony Brook University Season Opener | 2017 |
| 32 | 9:08.53 | Alexander GiffordStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2014 |
| 33 | 9:13.95 | Michael FamaStony Brook | Stony Brook | Stony Brook Snowflake Classic | 2022 |
| 34 | 9:14.19 | Brian TownsendWard Melville | Ward Melville '08 | Stony Brook University Track & Field Invitati | 2012 |
| 35 | 9:16.89 | Joseph AcitoStony Brook | Stony Brook | Stony Brook University Spring Opener | 2015 |
| 36 | 9:29.98 | Thomas FitzpatrickNorthport | Northport | Stony Brook University - Wolfie Invitational | 2018 |
| 37 | 9:30.49 | Jacob MarlinStony Brook | Stony Brook | Stony Brook University Spring Opener | 2015 |
| 38 | 9:38.95 | Justin TampelliniCommack | Commack '11 | Stony Brook University - Wolfie Invitational | 2014 |
| 39 | 10:08.51 | Matthew RathjeEastport-South Manor | Eastport-South Manor '22 | Stony Brook Snowflake Classic | 2025 |
| 40 | 11:01.03 | Lane 5Elwood / John Glenn | Elwood / John Glenn | Section XI State Qualifier | 2024 |
| 41 | 11:05.66 | Lane 8Northport | Northport | Section XI State Qualifier | 2024 |
| 42 | 11:14.94 | Lane 2Port Jefferson | Port Jefferson | Section XI State Qualifier | 2024 |
| 43 | 11:20.73 | Lane 1Hauppauge | Hauppauge | Section XI State Qualifier | 2024 |
| 44 | 11:42.61 | Drew DelisleSt. John the Baptist | St. John the Baptist | NSCHSAA/NSCHSGAA League Championships | 2024 |
