| 1 | 6:44.59 | Malcom DeCollibusChaminade | Chaminade '22 | NSCHSAA Varsity Spring Track Track & Field Championship | 2021 |
| 2 | 6:50.10 | Owen SweeneyChaminade | Chaminade '22 | NSCHSAA Varsity Spring Track Track & Field Championship | 2021 |
| 3 | 9:14.57 | Ryan McDermottChaminade | Chaminade '07 | Boys State Meet Results | 2006 |
| 4 | 9:28.81 | Michael KileyChaminade | Chaminade '09 | Saint Anthony's Invitational | 2009 |
| 5 | 9:30.45 | James SommerPlainedge | Plainedge '12 | Saint Anthony's Invitational | 2012 |
| 6 | 9:32.27 | Logan SchaefflerSanford H. Calhoun | Sanford H. Calhoun '24 | Section VIII State Qualifier | 2023 |
| 7 | 9:36.74 | Kevin McDermottChaminade | Chaminade '05 | NSCHSAA League Championships | 2005 |
| 8 | 9:40.34 | Chris AltamuraMacArthur | MacArthur | Saint Anthony's Invitational | 2009 |
| 9 | 9:41.88 | Thomas FruhaufManhasset | Manhasset '15 | Section VIII State Qualifier Meet | 2015 |
| 10 | 9:43.90 | Matthew RonanMassapequa | Massapequa '17 | Stony Brook University - Wolfie Invitational | 2018 |
| 11 | 9:44.01 | Brad KaufmannEast Meadow | East Meadow '13 | Section VIII Class County Championships | 2013 |
| 12 | 9:45.00 | Zachary TonerCalhoun | Calhoun '13 | Stony Brook University - Wolfie Invitational | 2016 |
| 13 | 9:45.16 | Myles MunroSeaford | Seaford '25 | Nassau Coaches Invitational | 2025 |
| 14 | 9:45.68 | Braeden JackelowManhasset | Manhasset '26 | Section VIII State Qualifier Day 2 | 2025 |
| 15 | 9:45.96 | Colin SeidlSacred Heart | Sacred Heart | Farmingdale State College Invitational | 2010 |
| 16 | 9:48.11 | Jose VelasquezJericho | Jericho '14 | Section VIII State Qualifier Meet | 2014 |
| 17 | 9:49.43 | Fredric LangMineola | Mineola '13 | Section VIII Class County Championships | 2013 |
| 18 | 9:49.74 | Owen StachlikWantagh | Wantagh '25 | Section 8 A County Championships | 2025 |
| 19 | 9:51.43 | Alex TosiOyster Bay | Oyster Bay '16 | Suffolk Coaches Meet | 2016 |
| 20 | 9:51.50 | William AndersonSyosset | Syosset '15 | Section VIII Class 3A County Championships | 2015 |
| 21 | 9:51.54 | Ryan WatsonManhasset | Manhasset '18 | Section VIII State Qualifier Meet | 2018 |
| 22 | 9:52.38 | Conor NickelChaminade | Chaminade '10 | NSCHSAA League Championships | 2009 |
| 23 | 9:53.00 | Ryan CliffordMacArthur | MacArthur '15 | Section VIII Class 3A County Championships | 2015 |
| 24 | 9:53.31 | Jonathan SchlothEast Rockaway | East Rockaway '14 | Section VIII State Qualifier Meet | 2014 |
| 25 | 9:53.87 | Justin SommerPlainedge | Plainedge '14 | Section VIII State Qualifier Meet | 2014 |
| 26 | 9:55.52 | Bradley KaufmannEast Meadow | East Meadow '13 | Saint Anthony's Invitational | 2012 |
| 27 | 9:56.18 | Ryan DepintoSyosset | Syosset '14 | Section VIII Class County Championships | 2013 |
| 28 | 9:56.81 | Christopher PerilloMepham | Mepham '16 | Saint Anthony's Invitational | 2016 |
| 29 | 9:57.30 | Sean TiernanFarmingdale | Farmingdale | Farmingdale State College Invitational | 2010 |
| 30 | 9:57.30 | Corey SquireWheatley | Wheatley '05 | UNIONRESULTS | 2005 |
| 31 | 9:57.56 | Lukas DerasmoPaul D. Schrieber / Port Washi | Paul D. Schrieber / Port Washi | Section VIII State Qualifier Day 2 | 2025 |
| 32 | 9:58.05 | Glenn LostrittoFriends Acad | Friends Acad '15 | Section VIII State Qualifier Meet | 2014 |
| 33 | 9:58.37 | Stije HuininkManhasset | Manhasset '25 | Section 8 State Qualifier | 2024 |
| 34 | 9:59.22 | Kevin CannonFloral Park Memorial | Floral Park Memorial | Section VIII State Qualifier | 2023 |
| 35 | 9:59.51 | Timothy CourtsManhasset | Manhasset '16 | Port Jefferson Steeplechase Invitational | 2016 |
| 36 | 10:00.36 | Steven MorraMacArthur | MacArthur '14 | Section VIII Class County Championships | 2014 |
| 37 | 10:01.64 | John WeedValley Stream Central | Valley Stream Central '15 | Section VIII Class County Championships | 2013 |
| 38 | 10:01.97 | John MahonJFK Bellmore | JFK Bellmore '14 | Section VIII Class County Championships | 2013 |
| 39 | 10:02.29 | Matthew WeilepManhasset | Manhasset '14 | Section VIII Class County Championships | 2014 |
| 40 | 10:03.25 | Evan SayreFriends Acad | Friends Acad '13 | Section VIII Class County Championships | 2013 |
| 41 | 10:03.37 | Francis O'BrienKellenberg | Kellenberg '18 | NSCHSAA League Championships | 2018 |
| 42 | 10:05.96 | Dale MittlemanSyosset | Syosset '14 | Section VIII Class County Championships | 2014 |
| 43 | 10:06.60 | Matt McgovernLong Beach | Long Beach '15 | Section VIII Class 3A County Championships | 2015 |
| 44 | 10:06.70 | Dan TullySyosset | Syosset '05 | UNIONRESULTS | 2005 |
| 45 | 10:07.67 | Jariq McNabFreeport | Freeport '22 | Section VIII County Championships Class AAA | 2022 |
| 46 | 10:07.83 | Patrick BurkeKellenberg | Kellenberg '10 | League Championships | 2010 |
| 47 | 10:07.90 | Charles DonnellyChaminade | Chaminade '08 | NSCHSAA League Championships | 2008 |
| 48 | 10:08.74 | Sean TullySyosset | Syosset '05 | Saint Anthony's Invitational | 2004 |
| 49 | 10:08.90 | Brendan BrethelLynbrook | Lynbrook '07 | Saint Anthony’s Invitational | |
| 50 | 10:09.3 | Arquimedes Dela CruzWantagh | Wantagh '09 | 2009 Nassau Coaches Invitational - Boys | |
| 51 | 10:09.87 | Joseph MiglioreChaminade | Chaminade '09 | NSCHSAA League Championships | 2009 |
| 52 | 10:09.89 | William NolanMepham | Mepham '15 | Section VIII Class County Championships | 2014 |
| 53 | 10:11.90 | Carter PatersonManhasset | Manhasset '15 | Section VIII State Qualifier Meet | 2014 |
| 54 | 10:12.68 | Peter KirgisPort Washington | Port Washington '16 | Saint Anthony's Invitational | 2015 |
| 55 | 10:12.71 | Alex GoldsteinGreat Neck North | Great Neck North '27 | Section 8 State Qualifier - Day 2 | 2026 |
| 56 | 10:13.40 | Kyle BirEast Meadow | East Meadow '25 | Section 8 AAA County Championship | 2025 |
| 57 | 10:13.49 | Christopher CourtsManhasset | Manhasset '19 | 47th Saint Anthony's Invitational | 2018 |
| 58 | 10:14.48 | Bryant BabelOceanside | Oceanside '14 | Section VIII State Qualifier Meet | 2014 |
| 59 | 10:14.69 | Jake TaverniteMineola | Mineola '14 | Stony Brook University - Wolfie Invitational | 2016 |
| 60 | 10:15.07 | Jared KimiabakhshGreat Neck North | Great Neck North '23 | Section VIII County Championships Class AA | 2022 |
| 61 | 10:15.70 | Steven TheodoropoulosPaul D. Schrieber / Port Washi | Paul D. Schrieber / Port Washi | Section VIII County Championships Class AAA | 2023 |
| 62 | 10:16.05 | Andrew TsimikalisManhasset | Manhasset '28 | Section 8 AA County Championship | 2026 |
| 63 | 10:16.10 | Milo ChristPaul D. Schrieber / Port Washi | Paul D. Schrieber / Port Washi '27 | Section 8 AAA County Championship | 2026 |
| 64 | 10:16.78 | David KnowlesManhasset | Manhasset '09 | Saint Anthony's Invitational | 2009 |
| 65 | 10:16.80 | Junseo DeschenesGreat Neck South | Great Neck South '24 | Section VIII County Championships Class AA | 2023 |
| 66 | 10:17.00 | Thomas ElnickKellenberg | Kellenberg '08 | NSCHSAA Spring Track & Field League Championships | 2006 |
| 67 | 10:17.15 | Michael TurnerMassapequa | Massapequa '19 | 47th Saint Anthony's Invitational | 2018 |
| 68 | 10:17.73 | Bryan VillafuerteEast Meadow | East Meadow '19 | Section VIII County Class 3A - Boyls | |
| 69 | 10:18.15 | Teddy HamlinOyster Bay | Oyster Bay '13 | Section VIII Class County Championships | 2013 |
| 70 | 10:19.33 | Michael ElnickKellenberg | Kellenberg '08 | SA Inv results 2 | |
| 71 | 10:19.33 | Patrick SmythFarmingdale | Farmingdale '19 | North Shore Invitational | 2018 |
| 72 | 10:19.69 | David RotkowitzValley Stream South | Valley Stream South '04 | Saint Anthony's Invitational | 2004 |
| 73 | 10:20.00 | Matthew BelmonteSanford H. Calhoun | Sanford H. Calhoun '23 | Section VIII County Championships Class AA | 2023 |
| 74 | 10:20.01 | Christopher SchimkusMassapequa | Massapequa '23 | Section VIII County Championships Class AAA | 2023 |
| 75 | 10:20.05 | Michael GordonValley Stream South | Valley Stream South '15 | Knight Time Invitational | 2014 |
| 76 | 10:20.11 | Jonah BerkowitzGreat Neck North | Great Neck North | Section 8 AA County Championship | 2025 |
| 77 | 10:20.26 | Jake CatalanoValley Stream North | Valley Stream North '16 | Section VIII Class 1A County Championships | 2015 |
| 78 | 10:20.95 | Brendan AbramsCalhoun | Calhoun '11 | Saint Anthony's Invitational | 2011 |
| 79 | 10:21.70 | Walter MendozaRoslyn | Roslyn '10 | Saint Anthony's Invitational | 2009 |
| 80 | 10:22.95 | Julian OsorioValley Stream North | Valley Stream North '15 | Section VIII Class 1A County Championships | 2015 |
| 81 | 10:23.11 | James SullivanKellenberg | Kellenberg '11 | Stony Brook University - Wolfie Invitational | 2017 |
| 82 | 10:23.31 | Jonah BerkowitzNorth Great Neck | North Great Neck | Section 8 State Qualifier | 2024 |
| 83 | 10:23.80 | Michael PuleioMassapequa | Massapequa '13 | Port Jefferson Steeplechase Invitational | 2012 |
| 84 | 10:24.37 | Eamon SheerinSyosset | Syosset '14 | Section VIII Class County Championships | 2014 |
| 85 | 10:24.68 | Scott CurtisSacred Heart | Sacred Heart | Stony Brook University - Wolfie Invitational | 2017 |
| 86 | 10:25.04 | Alex TulamoNorth Shore | North Shore | Port Jefferson Steeplechase Invitational | 2009 |
| 87 | 10:25.24 | Kyle WrynnEast Meadow | East Meadow '16 | Saint Anthony's Invitational | 2015 |
| 88 | 10:25.59 | Jack MatthewsEast Meadow | East Meadow '26 | Section 8 AAA County Championship | 2026 |
| 89 | 10:25.96 | Jacob EllenwoodSyosset | Syosset '27 | Section 8 AAA County Championship | 2026 |
| 90 | 10:26.09 | Dwight ClermontUniondale | Uniondale '14 | Knight Time Invitational | 2014 |
| 91 | 10:26.23 | Kevin TaylorPort Washington | Port Washington '22 | Section VIII County Championships Class AAA | 2022 |
| 92 | 10:26.29 | Aaron LiHicksville | Hicksville '19 | Suffolk Coaches Meet | 2019 |
| 93 | 10:26.45 | Shoki YamadaPort Washington | Port Washington '13 | Saint Anthony's Invitational | 2012 |
| 94 | 10:26.67 | Kyle FarinaVal Stream North | Val Stream North '29 | Section 8 A County Championship | 2026 |
| 95 | 10:26.82 | Christian CiciliaValley Stream North | Valley Stream North '20 | Section VIII County Class 1 A - Boys | |
| 96 | 10:26.82 | Kieran CookSouth Side | South Side '22 | Section VIII County Championships Class AA | 2022 |
| 97 | 10:26.89 | Michael SpinellaSeaford | Seaford '26 | Section 8 A County Championship | 2026 |
| 98 | 10:26.90 | Tim KramerMassapequa | Massapequa '06 | Saint Anthony’s Invitational | |
| 99 | 10:27.00 | Gregory MossKellenberg | Kellenberg '08 | SA Inv results 2 | |
| 100 | 10:27.00 | Dante DavisSouth Side | South Side '06 | Saint Anthony's Invitational | 2005 |
