| 1 | 15:56.30 | Mike BraniganNorthport | Northport '15 | Section XI Division XC Championships | 2012 |
| 2 | 15:57.10 | Ryan UdvadiaShoreham-Wading River | Shoreham-Wading River '14 | Section XI Division XC Championships | 2012 |
| 3 | 16:00.30 | Alex SaavedraSachem East | Sachem East '11 | Section XI Division Championships | 2010 |
| 4 | 16:01.59 | Dale SummervilleStony Brook | Stony Brook | Stony Brook University XC Invitational | 2004 |
| 5 | 16:03.54 | Mason GatewoodSt. Anthony's | St. Anthony's '18 | Saint Anthony's Cross Country Invitational | 2017 |
| 6 | 16:04.10 | Michael DamatoWalt Whitman | Walt Whitman '13 | Section XI Division XC Championships | 2012 |
| 7 | 16:04.45 | Jonathan LauerSachem North | Sachem North '17 | Section XI Boys Division XC Championships | 2016 |
| 8 | 16:06.25 | Bobby AndrewsShoreham-Wading River | Shoreham-Wading River '09 | Section XI Division Championships | 2008 |
| 9 | 16:08.30 | Kris MoranNorth Babylon | North Babylon '13 | Section XI Division XC Championships | 2012 |
| 10 | 16:09.40 | Zachary CammerWalt Whitman | Walt Whitman '13 | Section XI Division XC Championships | 2012 |
| 11 | 16:09.40 | Christopher TibbettsSachem North | Sachem North '17 | Section XI State Qualifier Meet | 2016 |
| 12 | 16:11.10 | Tim McGowanNorthport | Northport '14 | Section XI Division XC Championships | 2012 |
| 13 | 16:11.75 | Quinn RasemanWard Melville | Ward Melville '10 | Section XI Division Championships | 2008 |
| 14 | 16:12.61 | Mike BranniganNorthport | Northport '15 | Section XI Division XC Championships | 2013 |
| 15 | 16:14.20 | Ryan ColabellaHauppauge | Hauppauge '12 | Section XI Sectional Championships | 2011 |
| 16 | 16:15.00 | James DickinsonNorthport | Northport '13 | Section XI Division XC Championships | 2012 |
| 17 | 16:15.30 | Joe DiRienzoSachem East | Sachem East '12 | Section XI Division Championships | 2010 |
| 18 | 16:18.00 | James VallarWalt Whitman | Walt Whitman '13 | Section XI Division XC Championships | 2012 |
| 19 | 16:19.84 | Brendan ConnellSmithtown East | Smithtown East '09 | Section XI Division Championships | 2008 |
| 20 | 16:19.95 | RJ PleasantsHalf Hollow Hills East | Half Hollow Hills East '19 | Section XI Division XC Championships | 2018 |
| 21 | 16:20.45 | Chris PohlotShoreham-Wading River | Shoreham-Wading River '11 | Suffolk Coaches XC Invitational | 2009 |
| 22 | 16:20.75 | Nicholas DeFeliceSmithtown West | Smithtown West '19 | Section XI Division XC Championships | 2018 |
| 23 | 16:21.24 | Jason SantosSmithtown West | Smithtown West '09 | Section XI Sectional Championships | 2008 |
| 24 | 16:21.77 | Michael GrabowskiSmithtown West | Smithtown West '17 | Section XI State Qualifier Meet | 2016 |
| 25 | 16:22.43 | Robert KrauseConnetquot | Connetquot '06 | Section XI Division Championships | 2005 |
| 26 | 16:22.89 | Isaiah ClaiborneNorthport | Northport '18 | Section XI Boys Division XC Championships | 2017 |
| 27 | 16:24.30 | Ryan KutchSt. Anthony's | St. Anthony's '16 | NSCHSAA League Championships | 2015 |
| 28 | 16:24.97 | Christopher TibbetSachem North | Sachem North '17 | Section XI Division XC Championships | 2015 |
| 29 | 16:25.90 | Louis SantelliSt. Anthony's | St. Anthony's '14 | NSCHSAA League Championships | 2013 |
| 30 | 16:26.44 | Brian FarrellStony Brook | Stony Brook | Stony Brook University XC Invitational | 2004 |
| 31 | 16:27.84 | Thomas DilibertoSt. Anthony's | St. Anthony's '12 | NSCHSAA League Championships | 2010 |
| 32 | 16:28.55 | Mathew AlmondStony Brook | Stony Brook | Stony Brook University XC Invitational | 2004 |
| 33 | 16:29.30 | Dan DenisBayport-Blue Point | Bayport-Blue Point '10 | Section XI Division Championships | 2009 |
| 34 | 16:29.95 | James JoyWard Melville | Ward Melville '06 | Section XI Division Championships | 2005 |
| 35 | 16:30.12 | Patrick TuckerSt. Anthony's | St. Anthony's '15 | NSCHSAA League Championships | 2014 |
| 36 | 16:30.30 | Frank FezzaSachem North | Sachem North '09 | Section XI Sectional Championships | 2008 |
| 37 | 16:30.41 | John LeeShoreham-Wading River | Shoreham-Wading River '12 | Jim Smith Invitational | 2011 |
| 38 | 16:30.89 | Matthew PayampsSt. Anthony's | St. Anthony's '19 | Saint Anthony's Cross Country Invitational | 2018 |
| 39 | 16:31.10 | Frederick BuckholtzSt. Anthony's | St. Anthony's '16 | NSCHSAA League Championships | 2015 |
| 40 | 16:31.94 | Brendan MartinSmithtown West | Smithtown West '07 | Section XI Sectional Championships | 2005 |
| 41 | 16:32.15 | Joshua HadityCommack | Commack '15 | Section XI Division XC Championships | 2014 |
| 42 | 16:32.42 | Kal LewisShelter Island | Shelter Island '20 | Section XI Boys Division XC Championships | 2017 |
| 43 | 16:32.69 | Thomas CirritoMiller Place | Miller Place '20 | Section XI Division XC Championships | 2018 |
| 44 | 16:32.82 | Dan O'ConnorNorthport | Northport '18 | Section XI Boys Division XC Championships | 2017 |
| 45 | 16:33.15 | Austin ConeysHarborfields | Harborfields '12 | Saint Anthony's Cross Country Invitational | 2011 |
| 46 | 16:33.50 | Thomas MeehanEastport-South Manor | Eastport-South Manor '14 | Section XI Division XC Championships | 2012 |
| 47 | 16:34.15 | Kevin CawleySmithtown East | Smithtown East '19 | Section XI Division XC Championships | 2018 |
| 48 | 16:34.70 | Zach KrauseConnetquot | Connetquot '11 | Section XI Sectional Championships | 2010 |
| 49 | 16:35.90 | Alex KramerNorthport | Northport '13 | Section XI Division XC Championships | 2012 |
| 50 | 16:36.28 | Erik EngstromEast Hampton | East Hampton '16 | Section XI Division XC Championships | 2015 |
| 51 | 16:36.70 | Nick HirdtMiller Place | Miller Place '13 | Section XI Division XC Championships | 2012 |
| 52 | 16:37.50 | Mike WattsIslip | Islip '14 | Section XI Division XC Championships | 2012 |
| 53 | 16:37.90 | Tyler MurthaConnetquot | Connetquot '11 | Section XI Sectional Championships | 2010 |
| 54 | 16:38.06 | Patrick GintySmithtown East | Smithtown East '13 | NSCHSAA League Championships | 2012 |
| 55 | 16:41.30 | Connor CrowleyBayport-Blue Point | Bayport-Blue Point '11 | Section XI Division Championships | 2010 |
| 56 | 16:41.52 | Kevin FoleyCommack | Commack '17 | Section XI Division XC Championships | 2015 |
| 57 | 16:42.18 | Jack RyanWesthampton Beach | Westhampton Beach '17 | Section XI State Qualifier Meet | 2016 |
| 58 | 16:42.57 | Nicholas CipollaSmithtown West | Smithtown West '18 | Section XI Boys Division XC Championships | 2017 |
| 59 | 16:42.60 | Ryan ScarpelliSachem East | Sachem East '12 | Section XI Division Championships | 2011 |
| 60 | 16:42.80 | Shaun KrawitzStony Brook | Stony Brook | Stony Brook University XC Invitational | 2004 |
| 61 | 16:43.23 | Colin AndersonNorthport | Northport '09 | Section XI Division Championships | 2008 |
| 62 | 16:43.57 | Sean RyanNorthport | Northport '19 | Section XI Boys Division XC Championships | 2017 |
| 63 | 16:43.87 | James BurkePort Jefferson | Port Jefferson '15 | Jim Smith Invitational | 2014 |
| 64 | 16:44.17 | Ryan ScanlonHarborfields | Harborfields '16 | Section XI Division XC Championships | 2015 |
| 65 | 16:44.60 | Vincent CicaleWard Melville | Ward Melville '13 | Section XI Division XC Championships | 2012 |
| 66 | 16:44.90 | Kyle KellyWest Islip | West Islip '16 | Section XI Division XC Championships | 2015 |
| 67 | 16:44.91 | Adam LaFeminaBayport-Blue Point | Bayport-Blue Point '13 | Suffolk Coaches Invitational | 2012 |
| 68 | 16:45.13 | Gavin EhlersWesthampton Beach | Westhampton Beach '22 | 49th Saint Anthony's Cross Country Invitational | 2019 |
| 69 | 16:45.42 | Frederick BuckholtSt. Anthony's | St. Anthony's '16 | Saint Anthony's Cross Country Invitational | 2015 |
| 70 | 16:45.93 | Skyler LattucaLongwood | Longwood '17 | Section XI Division XC Championships | 2015 |
| 71 | 16:47.74 | Cabel McCandlessLindenhurst | Lindenhurst '16 | Section XI Division XC Championships | 2015 |
| 72 | 16:48.49 | Geoff EngelMiller Place | Miller Place '09 | Section XI Division Championships | 2008 |
| 73 | 16:48.66 | Joe ParksDeer Park | Deer Park '06 | Section XI Division Championships | 2005 |
| 74 | 16:48.67 | Steven SpreizerSmithtown West | Smithtown West '18 | Section XI Boys Division XC Championships | 2017 |
| 75 | 16:48.76 | Evan BloombergNorthport | Northport '09 | Section XI Sectional Championships | 2008 |
| 76 | 16:48.96 | Ryan DearieSt. Anthony's | St. Anthony's '16 | Saint Anthony's Cross Country Invitational | 2015 |
| 77 | 16:49.00 | Scott LittsConnetquot | Connetquot '11 | Section XI Sectional Championships | 2010 |
| 78 | 16:49.20 | Jeremy MiekleyMiller Place | Miller Place '14 | Section XI Division XC Championships | 2012 |
| 79 | 16:49.54 | Justin AlloneSachem East | Sachem East '18 | Section XI Boys Division XC Championships | 2017 |
| 80 | 16:49.81 | Daniel FrostSmithtown West | Smithtown West '07 | Section XI Division Championships | 2005 |
| 81 | 16:50.16 | Elijah ClaiborneNorthport | Northport '18 | Section XI Boys Division XC Championships | 2017 |
| 82 | 16:50.22 | Matthew KatzHarborfields | Harborfields '17 | Section XI Boys Division XC Championships | 2016 |
| 83 | 16:50.27 | James HuntShoreham-Wading River | Shoreham-Wading River '10 | Suffolk Coaches XC Invitational | 2009 |
| 84 | 16:50.67 | Kyle WightmanShoreham-Wading River | Shoreham-Wading River '09 | Section XI Division Championships | 2008 |
| 85 | 16:50.79 | Thomas BrockBellport | Bellport '18 | Section XI Boys Division XC Championships | 2016 |
| 86 | 16:51.00 | Aiden SmythWalt Whitman | Walt Whitman '18 | Section XI Boys Division XC Championships | 2017 |
| 87 | 16:51.19 | Chris NienburgWard Melville | Ward Melville '19 | Section XI Boys Division XC Championships | 2017 |
| 88 | 16:51.20 | Michael DanziSmithtown West | Smithtown West '20 | Section XI Division XC Championships | 2018 |
| 89 | 16:51.40 | Liam KellyConnetquot | Connetquot '14 | Section XI Division XC Championships | 2012 |
| 90 | 16:51.65 | Matthew ViscosiWard Melville | Ward Melville '17 | Section XI State Qualifier Meet | 2016 |
| 91 | 16:51.85 | John OnkenSachem North | Sachem North '15 | Suffolk Officials XC Invitational | 2014 |
| 92 | 16:52.00 | Timothy OdinNorthport | Northport '11 | Section XI Sectional Championships | 2010 |
| 93 | 16:52.06 | Dominick De MatteoHalf Hollow Hills West | Half Hollow Hills West '09 | Section XI Sectional Championships | 2008 |
| 94 | 16:53.30 | Tyler KeysShoreham-Wading River | Shoreham-Wading River '12 | Section XI Sectional Championships | 2011 |
| 95 | 16:54.30 | Ben TuttleEastport-South Manor | Eastport-South Manor '11 | Section XI Division Championships | 2010 |
| 96 | 16:54.39 | Carlos SantosPatchogue-Medford | Patchogue-Medford '18 | Section XI Boys Division XC Championships | 2016 |
| 97 | 16:54.59 | Ryan CorbettEastport-South Manor | Eastport-South Manor '17 | Section XI State Qualifier Meet | 2016 |
| 98 | 16:54.67 | Daniel ConnellyMount Sinai | Mount Sinai '14 | Section XI Division XC Championships | 2013 |
| 99 | 16:54.82 | David CabelloSmithtown West | Smithtown West '19 | Section XI Boys Division XC Championships | 2017 |
| 100 | 16:55.10 | Dom CostanzoConnetquot | Connetquot '11 | Section XI Sectional Championships | 2010 |
