| 1 | 6:08.86 | Thomas DilibertoSt. Anthony's | St. Anthony's '12 | Port Jefferson Steeplechase Invitational | 2011 |
| 2 | 6:09.10 | Erik EngstromEast Hampton | East Hampton '16 | Suffolk Officials Meet | 2016 |
| 3 | 6:15.28 | Patrick KainSt. John the Baptist | St. John the Baptist '18 | Port Jefferson Steeplechase Invitational | 2016 |
| 4 | 6:16.97 | Ken WalshakSt. Anthony's | St. Anthony's | Port Jefferson Steeplechase Invitational | 2010 |
| 5 | 6:17.70 | Brian SmithSt. Anthony's | St. Anthony's '12 | Eastern States Invitational | 2011 |
| 6 | 6:18.49 | Joe RayBayport-Blue Point | Bayport-Blue Point '11 | Port Jefferson Steeplechase Invitational | 2011 |
| 7 | 6:19.63 | Cole ContePort Jefferson | Port Jefferson '12 | Port Jefferson Steeplechase Invitational | 2011 |
| 8 | 6:20.10 | James MurphyPort Jefferson | Port Jefferson '15 | Stony Brook University Spring Opener | 2014 |
| 9 | 6:20.76 | Gregory BaldinucciConnetquot | Connetquot '24 | Long Island Meet of Champions at St. Anthonys | 2022 |
| 10 | 6:21.46 | Thomas MeehanEastport-South Manor | Eastport-South Manor '14 | Port Jefferson Steeplechase Invitational | 2013 |
| 11 | 6:21.55 | John AntonacciBayport-Blue Point | Bayport-Blue Point '13 | Port Jefferson Steeplechase Invitational | 2011 |
| 12 | 6:21.57 | Keith SteinbrecherShoreham-Wading River | Shoreham-Wading River '14 | Port Jefferson Steeplechase Invitational | 2014 |
| 13 | 6:21.67 | Nicholas KaufmannSt. Anthony's | St. Anthony's '11 | Eastern States Invitational | 2011 |
| 14 | 6:22.39 | Joseph TuckerSt. Anthony's | St. Anthony's '15 | Port Jefferson Steeplechase Invitational | 2013 |
| 15 | 6:23.28 | Justin JulichPort Jefferson | Port Jefferson '16 | Port Jefferson Steeplechase Invitational | 2016 |
| 16 | 6:23.43 | Nicholas DeFeliceSmithtown West | Smithtown West '19 | Port Jefferson Steeplechase Invitational | 2018 |
| 17 | 6:23.54 | James BurkePort Jefferson | Port Jefferson '15 | Port Jefferson Steeplechase Invitational | 2012 |
| 18 | 6:23.60 | Jake HenslerSt. Anthony's | St. Anthony's '13 | Eastern States Invitational | 2011 |
| 19 | 6:25.64 | Tyler MurthaConnetquot | Connetquot '11 | Port Jefferson Steeplechase Invitational | 2011 |
| 20 | 6:25.74 | Frank SegretoSt. Anthony's | St. Anthony's '12 | Port Jefferson Steeplechase Invitational | 2011 |
| 21 | 6:25.80 | Jack RyanWesthampton Beach | Westhampton Beach '17 | Port Jefferson Steeplechase Invitational | 2017 |
| 22 | 6:25.87 | Frederick BuckholtzSt. Anthony's | St. Anthony's '16 | Port Jefferson Steeplechase Invitational | 2015 |
| 23 | 6:26.00 | Aidan HealySt. John the Baptist | St. John the Baptist '18 | Port Jefferson Steeplechase Invitational | 2017 |
| 24 | 6:26.24 | Robert CherkisSt. Anthony's | St. Anthony's '09 | Port Jefferson Steeplechase Invitational | 2009 |
| 25 | 6:26.42 | John McMullinSt. Anthony's | St. Anthony's '14 | Port Jefferson Steeplechase Invitational | 2013 |
| 26 | 6:27.60 | Connor CrowleyBayport-Blue Point | Bayport-Blue Point '11 | Port Jefferson Steeplechase Invitational | 2011 |
| 27 | 6:27.76 | Steven GalvaoMiddle Country | Middle Country '10 | Port Jefferson Steeplechase Invitational | 2010 |
| 28 | 6:28.95 | Matthew MaidhofSmithtown West | Smithtown West '18 | Don Scott Memorial Relays | 2018 |
| 29 | 6:29.25 | Matt ZamparielloSt. John the Baptist | St. John the Baptist '11 | Port Jefferson Steeplechase Invitational | 2011 |
| 30 | 6:30.55 | Ryan IoccaConnetquot | Connetquot '22 | Long Island Meet of Champions at St. Anthonys | 2022 |
| 31 | 6:31.69 | Christian ReedEast Islip | East Islip '10 | Port Jefferson Steeplechase Invitational | 2010 |
| 32 | 6:32.19 | Chris SwensonBellport | Bellport '14 | Port Jefferson Steeplechase Invitational | 2013 |
| 33 | 6:32.40 | Carlos SantosPatchogue-Medford | Patchogue-Medford '18 | Suffolk Officials Meet | 2016 |
| 34 | 6:32.51 | Brian KreiderSt. Anthony's | St. Anthony's '14 | Post Easter Classic | 2014 |
| 35 | 6:32.86 | Zach LeCatesRocky Point | Rocky Point '11 | Port Jefferson Steeplechase Invitational | 2011 |
| 36 | 6:33.04 | Matthew BlauveltSmithtown East | Smithtown East '17 | Port Jefferson Steeplechase Invitational | 2017 |
| 37 | 6:33.51 | Charles HetterichWest Islip | West Islip '16 | Port Jefferson Steeplechase Invitational | 2014 |
| 38 | 6:34.32 | Drew DillinghamRiverhead | Riverhead '08 | Port Jefferson Steeplechase | 2008 |
| 39 | 6:34.42 | Nick TermineNorthport | Northport '14 | Longwood Frosh/Soph Championships | 2012 |
| 40 | 6:35.17 | Daniel SierraEast Islip | East Islip '08 | Port Jefferson Steeplechase | 2008 |
| 41 | 6:35.19 | Robert VetriBayport-Blue Point | Bayport-Blue Point '13 | Port Jefferson Steeplechase Invitational | 2012 |
| 42 | 6:35.29 | Nicholas BrennanSt. Anthony's | St. Anthony's '10 | Port Jefferson Steeplechase Invitational | 2010 |
| 43 | 6:35.89 | Liam KellyConnetquot | Connetquot '14 | Port Jefferson Steeplechase Invitational | 2013 |
| 44 | 6:36.50 | Joe BattagliaSachem East | Sachem East '14 | Suffolk Officials Meet | 2014 |
| 45 | 6:36.71 | Robert CalamiaSmithtown East | Smithtown East '12 | Longwood Frosh/Soph Championships | 2010 |
| 46 | 6:37.01 | John BlacklerSt. John the Baptist | St. John the Baptist '09 | Port Jefferson Steeplechase Invitational | 2009 |
| 47 | 6:38.00 | Matthew PatsySachem East | Sachem East '16 | Suffolk Officials Meet | 2016 |
| 48 | 6:38.30 | Kevin CorriganSt. Anthony's | St. Anthony's '08 | Post Easter Classic | 2008 |
| 49 | 6:38.36 | Alex RebicPort Jefferson | Port Jefferson '18 | Port Jefferson Steeplechase Invitational | 2017 |
| 50 | 6:38.80 | John KaplanBayport-Blue Point | Bayport-Blue Point '14 | Suffolk Officials Meet | 2014 |
| 51 | 6:39.00 | Tory CangeMiddle Country | Middle Country '08 | Port Jefferson Steeplechase | 2008 |
| 52 | 6:39.30 | Colin KernNorthport | Northport '13 | Suffolk Officials Meet | 2012 |
| 53 | 6:39.37 | James O'BrienSt. John the Baptist | St. John the Baptist '16 | Suffolk Coaches Meet | 2016 |
| 54 | 6:39.52 | Griffin KudlaSt. Anthony's | St. Anthony's '20 | Boys Freshmen - Sophomore Championships | 2018 |
| 55 | 6:39.71 | Ryan FowkesEast Hampton | East Hampton '19 | Port Jefferson Steeplechase Invitational | 2018 |
| 56 | 6:39.83 | Thomas FlynnSt. Anthony's | St. Anthony's '11 | Port Jefferson Steeplechase Invitational | 2010 |
| 57 | 6:39.83 | Juan LassoWesthampton Beach | Westhampton Beach '19 | Port Jefferson Steeplechase Invitational | 2017 |
| 58 | 6:39.98 | Kyle KellyWest Islip | West Islip '16 | Longwood Frosh/Soph Championships | 2014 |
| 59 | 6:40.00 | Zachary LaneWard Melville | Ward Melville '14 | Saint Anthony's Invitational | 2012 |
| 60 | 6:40.28 | Liam CurleySt. Anthony's | St. Anthony's '25 | NSCHSAA/NSCHSGAA League Championships | 2024 |
| 61 | 6:40.30 | Daniel CameronWest Islip | West Islip '16 | Longwood Frosh/Soph Championships | 2014 |
| 62 | 6:40.80 | A. TylerSt. Anthony's | St. Anthony's '14 | Boys Freshmen - Sophomore Championships | 2012 |
| 63 | 6:41.18 | Devin LaudenschlagSt. John the Baptist | St. John the Baptist '16 | Port Jefferson Steeplechase Invitational | 2016 |
| 64 | 6:41.20 | Thomas FodorNorthport | Northport '20 | Port Jefferson Steeplechase Invitational | 2018 |
| 65 | 6:41.20 | Emilo EspinozaEast Hampton | East Hampton '18 | Suffolk Officials Meet | 2016 |
| 66 | 6:41.60 | Amani MorrellSt. Anthony's | St. Anthony's '18 | Boys Freshmen - Sophomore Championships | 2016 |
| 67 | 6:41.79 | Peter DeMaioSt. John the Baptist | St. John the Baptist '17 | Port Jefferson Steeplechase Invitational | 2016 |
| 68 | 6:41.87 | Nick BeglaneHauppauge | Hauppauge '16 | Port Jefferson Steeplechase Invitational | 2014 |
| 69 | 6:42.20 | Rory HanniganSt. John the Baptist | St. John the Baptist '15 | Port Jefferson Steeplechase Invitational | 2014 |
| 70 | 6:42.38 | Cameron JacobsNorthport | Northport '17 | Longwood Frosh/Soph Championships | 2015 |
| 71 | 6:42.44 | Kyle WightmanShoreham-Wading River | Shoreham-Wading River '09 | Suffolk Coaches Meet | 2008 |
| 72 | 6:43.05 | Patrick KutchSt. Anthony's | St. Anthony's '18 | Eastern States Invitational | 2017 |
| 73 | 6:43.41 | Cody AmengualWest Babylon | West Babylon '10 | Port Jefferson Steeplechase Invitational | 2009 |
| 74 | 6:43.50 | Jamison SherrettsNorth Babylon | North Babylon '14 | Port Jefferson Steeplechase Invitational | 2013 |
| 75 | 6:43.57 | Devin LaudenschlagerSt. John the Baptist | St. John the Baptist '16 | Port Jefferson Steeplechase Invitational | 2015 |
| 76 | 6:43.60 | Vincent MeliaWest Islip | West Islip '12 | Port Jefferson Steeplechase Invitational | 2012 |
| 77 | 6:44.00 | Matthew KahnPort Jefferson | Port Jefferson '08 | Port Jefferson Steeplechase | 2008 |
| 78 | 6:44.72 | Sam WalkerPort Jefferson | Port Jefferson '18 | Port Jefferson Steeplechase Invitational | 2017 |
| 79 | 6:44.80 | Marc WeilandicsLongwood | Longwood '11 | Longwood Frosh/Soph Championships | 2009 |
| 80 | 6:44.80 | Nick DestefanoMiddle Country | Middle Country '09 | Port Jefferson Steeplechase | 2008 |
| 81 | 6:44.81 | Greg HorbatiukWesthampton Beach | Westhampton Beach '13 | Saint Anthony's Invitational | 2012 |
| 82 | 6:45.20 | Alex HarveyKings Park | Kings Park '14 | Suffolk Officials Meet | 2014 |
| 83 | 6:45.23 | John O'ConnellSt. John the Baptist | St. John the Baptist '20 | Boys Freshmen - Sophomore Championships | 2018 |
| 84 | 6:45.35 | Kevin SullivanPort Jefferson | Port Jefferson '10 | Port Jefferson Steeplechase Invitational | 2009 |
| 85 | 6:45.79 | Jacob OconBayport-Blue Point | Bayport-Blue Point '17 | Port Jefferson Steeplechase Invitational | 2016 |
| 86 | 6:45.93 | Craig NelsonWest Islip | West Islip '14 | Longwood Frosh/Soph Championships | 2012 |
| 87 | 6:45.96 | Anthony DiLorenzoConnetquot | Connetquot '28 | Suffolk Frosh Soph Boys | 2026 |
| 88 | 6:46.10 | Bryan ReillySt. John the Baptist | St. John the Baptist '14 | Suffolk Officials Meet | 2014 |
| 89 | 6:48.77 | Pat FannonWest Islip | West Islip '09 | Port Jefferson Steeplechase Invitational | 2009 |
| 90 | 6:48.98 | Declan BrownSt. John the Baptist | St. John the Baptist '17 | Port Jefferson Steeplechase Invitational | 2016 |
| 91 | 6:49.03 | Michael RicciardelliCommack | Commack '15 | Suffolk Coaches Meet | 2015 |
| 92 | 6:49.10 | Sean NorbergShoreham-Wading River | Shoreham-Wading River '08 | Longwood Frosh/Soph Championships | 2006 |
| 93 | 6:49.35 | Edward GibbonsBellport | Bellport '12 | Suffolk Officials Meet | 2010 |
| 94 | 6:49.60 | Tyler HayesKings Park | Kings Park '16 | Suffolk Officials Meet | 2016 |
| 95 | 6:49.74 | Kevin MossSt. John the Baptist | St. John the Baptist '16 | Port Jefferson Steeplechase Invitational | 2015 |
| 96 | 6:49.83 | Robert KellyConnetquot | Connetquot '13 | Longwood Frosh/Soph Championships | 2011 |
| 97 | 6:49.90 | Jeremy FeinsteinCommack | Commack '14 | Longwood Frosh/Soph Championships | 2012 |
| 98 | 6:50.20 | Lee NicholsonComsewogue | Comsewogue '18 | Suffolk Officials Meet | 2016 |
| 99 | 6:50.35 | Daniel O'DonovanBay Shore | Bay Shore '18 | Longwood Frosh/Soph Championships | 2015 |
| 100 | 6:50.51 | Daniel BlockSachem North | Sachem North '15 | Port Jefferson Steeplechase Invitational | 2013 |
