| 1 | 14:51.69 | Nick CruzStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2018 |
| 2 | 14:52.90 | Nicholas LemonStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2014 |
| 3 | 14:54.62 | Greg MangarelliStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2018 |
| 4 | 14:56.13 | Brendan McCarthyMiller Place | Miller Place '11 | Stony Brook University - Wolfie Invitational | 2014 |
| 5 | 14:56.53 | Mitchell KunStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2015 |
| 6 | 15:01.35 | Benjamin McDermottStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2018 |
| 7 | 15:14.11 | Bryce HedmanStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2017 |
| 8 | 15:16.11 | Joshua HadityCommack | Commack '15 | Stony Brook University - Wolfie Invitational | 2017 |
| 9 | 15:25.61 | Victor GarifoBayport-Blue Point | Bayport-Blue Point '16 | Stony Brook University - Wolfie Invitational | 2017 |
| 10 | 15:31.08 | Daniel ConnellyMount Sinai | Mount Sinai '14 | Stony Brook University - Wolfie Invitational | 2015 |
| 11 | 15:34.34 | Kevin VinolasStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2016 |
| 12 | 15:38.64 | Matthew LeeStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2014 |
| 13 | 15:42.92 | Joseph AcitoStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2016 |
| 14 | 15:55.51 | Eamonn BeersSt. Anthony's | St. Anthony's '15 | Stony Brook University - Wolfie Invitational | 2018 |
| 15 | 16:14.68 | Brendan FoleyStony Brook | Stony Brook | Stony Brook University - Wolfie Invitational | 2018 |
| 16 | 16:20.30 | James O'BrienSt. John the Baptist | St. John the Baptist '16 | Skyline Track & Field Championships | 2018 |
| 17 | 16:20.62 | Tyler McNamaraSachem North | Sachem North '15 | Stony Brook University - Wolfie Invitational | 2016 |
| 18 | 16:31.62 | Ryan HaunBayport-Blue Point | Bayport-Blue Point '15 | Skyline Track & Field Championships | 2018 |
| 19 | 16:46.78 | Shane MartensenEast Islip | East Islip '13 | St. Joseph College | 2014 |
| 20 | 17:10.45 | John SeskusCommack | Commack '12 | St. Joseph College | 2014 |
| 21 | 17:13.68 | Brian CoyleBayport-Blue Point | Bayport-Blue Point '09 | Farmingdale State College Invitational | 2010 |
| 22 | 17:16.20 | Kenneth BarrettEastport-South Manor | Eastport-South Manor | Skyline Conference Track & Field Championships | 2021 |
| 23 | 17:16.33 | Tom RuppelSachem East | Sachem East '13 | Coach Omeltchenko Open | 2014 |
| 24 | 17:25.47 | Matthew GoidellSt. John the Baptist | St. John the Baptist '12 | Coach Omeltchenko Open | 2014 |
| 25 | 18:23.92 | John SuchoparConnetquot | Connetquot '12 | St. Joseph College | 2014 |
| 26 | 18:28.69 | Shane AcostaPatchogue-Medford | Patchogue-Medford '12 | St. Joseph College | 2014 |
| 27 | 18:29.73 | Patrick MurphySt. Anthony's | St. Anthony's '10 | Binghamton Banana Relays | 2025 |
| 28 | 18:48.23 | Joseph SanelliJohn Glenn | John Glenn '21 | Binghamton Banana Relays | 2025 |
| 29 | 18:55.67 | Chris KitoComsewogue | Comsewogue '06 | coms 5k mw | 2006 |
| 30 | 19:32.68 | Ray TurnerComsewogue | Comsewogue '07 | coms 5k mw | 2006 |
| 31 | 19:44.35 | Nicholas ReyesMiddle Country | Middle Country '20 | Skyline Conference Track & Field Championships | 2021 |
| 32 | 22:08.25 | Anthony FitzgeraldWest Babylon | West Babylon '20 | Skyline Conference Track & Field Championships | 2021 |
