| 1 | 15:25.36 | Brian FarrellStony Brook | Stony Brook | SBU XC06 Boys Results | 2006 |
| 2 | 15:40.18 | Alex FelceStony Brook | Stony Brook | SBU XC06 Boys Results | 2006 |
| 3 | 15:44.98 | Mike BranniganNorthport | Northport '15 | Section XI Cross Country County Championships | 2014 |
| 4 | 15:46.60 | Kevin TschirhartNorthport | Northport '05 | Section XI Cross Country | 2004 |
| 5 | 15:47.00 | Ryan SheridanWalt Whitman | Walt Whitman '07 | Section XI Cross Country | 2004 |
| 6 | 16:03.79 | Iain WhitfieldStony Brook | Stony Brook | SBU XC06 Boys Results | 2006 |
| 7 | 16:14.06 | Mike PetrinaStony Brook | Stony Brook | SBU XC06 Boys Results | 2006 |
| 8 | 16:22.88 | Kevin McCarthyStony Brook | Stony Brook | SBU XC06 Boys Results | 2006 |
| 9 | 16:24.85 | Robert FlemingSt. Anthony's | St. Anthony's '06 | SBU XC06 Boys Results | 2006 |
| 10 | 16:25.00 | Robert KrauseConnetquot | Connetquot '06 | Section XI Cross Country | 2004 |
| 11 | 16:25.22 | James JohnstonLongwood | Longwood '06 | Hofstra Men's XC Invitational 2006 | |
| 12 | 16:26.00 | John KeenanSt. Anthony's | St. Anthony's '05 | SBU XC06 Boys Results | 2006 |
| 13 | 16:26.84 | Ryan UdvadiaShoreham-Wading River | Shoreham-Wading River '14 | Section XI Cross Country County Championships | 2013 |
| 14 | 16:27.63 | Giovanni SignorettiSmithtown West | Smithtown West '08 | 2007 Division XC Boys Results | |
| 15 | 16:27.69 | Daniel FrostSmithtown West | Smithtown West '07 | 2006 Section XI SQ Boys XC Results | |
| 16 | 16:28.33 | Kyle MerberHalf Hollow Hills West | Half Hollow Hills West '08 | 2006 Section XI SQ Boys XC Results | |
| 17 | 16:28.43 | Michael DanziSmithtown West | Smithtown West '20 | Section XI State Qualifier Meet | 2019 |
| 18 | 16:29.43 | Michael SilveriEastport-South Manor | Eastport-South Manor '21 | Section XI State Qualifier Meet | 2019 |
| 19 | 16:31.92 | Tim McGowanNorthport | Northport '14 | Section XI Cross Country County Championships | 2013 |
| 20 | 16:35.0 | Dave JohnsonWalt Whitman | Walt Whitman | Nassau County Coaches Association Cross Country Invitational | 2001 |
| 21 | 16:35.74 | Isaiah ClaiborneNorthport | Northport '18 | Section XI State Qualifier Meet | 2017 |
| 22 | 16:36.26 | Joshua HadityCommack | Commack '15 | Section XI Cross Country County Championships | 2014 |
| 23 | 16:36.60 | Ryan HaysShoreham-Wading River | Shoreham-Wading River '05 | Section XI Cross Country | 2004 |
| 24 | 16:38.54 | Jack McGowanNorthport | Northport '14 | Section XI Cross Country County Championships | 2013 |
| 25 | 16:39.62 | Steven SpreizerSmithtown West | Smithtown West '18 | Section XI State Qualifier Meet | 2017 |
| 26 | 16:41.41 | Derek RammelkampMiller Place | Miller Place '07 | 2006 Section XI SQ Boys XC Results | |
| 27 | 16:42.31 | John OnkenSachem North | Sachem North '15 | Section XI Cross Country County Championships | 2014 |
| 28 | 16:42.41 | Jonathon CuomoWilliam Floyd | William Floyd '08 | 2007 Division XC Boys Results | |
| 29 | 16:42.8 | Andrew KnipfingMiller Place | Miller Place | Nassau County Coaches Association Cross Country Invitational | 2001 |
| 30 | 16:42.96 | Trevor GuerreraSachem East | Sachem East '14 | Section XI Cross Country County Championships | 2013 |
| 31 | 16:43.1 | Ryan ShonMiller Place | Miller Place '05 | Nassau County Coaches Association Cross Country Invitational | 2004 |
| 32 | 16:43.26 | Thomas MeehanEastport-South Manor | Eastport-South Manor '14 | Section XI Cross Country County Championships | 2013 |
| 33 | 16:43.54 | Bobby AndrewsShoreham-Wading River | Shoreham-Wading River '09 | 2007 Division XC Boys Results | |
| 34 | 16:43.98 | Thomas FodorNorthport | Northport '20 | Section XI State Qualifier Meet | 2019 |
| 35 | 16:44.54 | RJ PleasantsHalf Hollow Hills East | Half Hollow Hills East '19 | Section XI State Qualifier Meet | 2018 |
| 36 | 16:45.53 | Brendan MartinSmithtown West | Smithtown West '07 | 2006 Section XI SQ Boys XC Results | |
| 37 | 16:46.00 | Geary GubbinsSouthampton | Southampton '05 | Section XI Cross Country | 2004 |
| 38 | 16:46.17 | Daniel SabiaSmithtown West | Smithtown West '20 | Section XI State Qualifier Meet | 2019 |
| 39 | 16:46.72 | Nicholas DeFeliceSmithtown West | Smithtown West '19 | Section XI State Qualifier Meet | 2017 |
| 40 | 16:46.75 | Anthony CocciaSachem North | Sachem North '14 | Section XI Cross Country County Championships | 2013 |
| 41 | 16:47.60 | Greg CantwellWard Melville | Ward Melville '05 | Section XI Cross Country | 2004 |
| 42 | 16:48.48 | Justin LeopoldNorthport | Northport '14 | Section XI Cross Country County Championships | 2013 |
| 43 | 16:48.60 | John RipaWard Melville | Ward Melville '15 | Section XI Cross Country County Championships | 2014 |
| 44 | 16:48.66 | Alex SaavedraSachem East | Sachem East '11 | Suffolk PAL Invitational | 2008 |
| 45 | 16:49.93 | Kevin CawleySmithtown East | Smithtown East '19 | Section XI State Qualifier Meet | 2018 |
| 46 | 16:50.80 | Quinn RasemanWard Melville | Ward Melville '10 | Jim Smith Invitational | 2008 |
| 47 | 16:50.82 | Nick TermineNorthport | Northport '14 | Section XI Cross Country County Championships | 2013 |
| 48 | 16:52.21 | Barry FranklinLongwood | Longwood '08 | 2007 Division XC Boys Results | |
| 49 | 16:52.23 | Carlos SantosPatchogue-Medford | Patchogue-Medford '18 | Section XI State Qualifier Meet | 2017 |
| 50 | 16:52.50 | James JoyWard Melville | Ward Melville '06 | Section XI Cross Country | 2004 |
| 51 | 16:53.44 | Aidar MatthewsNorthport | Northport '21 | Section XI State Qualifier Meet | 2019 |
| 52 | 16:53.90 | Justin CurtisWesthampton Beach | Westhampton Beach '06 | Section XI Cross Country | 2004 |
| 53 | 16:54.01 | Matthew FloodEastport-South Manor | Eastport-South Manor '21 | Section XI State Qualifier Meet | 2019 |
| 54 | 16:54.46 | Daniel CzopCommack | Commack '19 | Section XI State Qualifier Meet | 2018 |
| 55 | 16:54.67 | Elijah ClaiborneNorthport | Northport '18 | Section XI State Qualifier Meet | 2017 |
| 56 | 16:54.78 | Isaac Garcia-CassaniSachem North | Sachem North '14 | Section XI Cross Country County Championships | 2013 |
| 57 | 16:55.60 | Matthew GladyszShoreham-Wading River | Shoreham-Wading River '15 | Section XI Cross Country County Championships | 2014 |
| 58 | 16:56.32 | Frank FezzaSachem North | Sachem North '09 | Jim Smith Invitational | 2008 |
| 59 | 16:56.50 | Timothy KeeganSt. Anthony's | St. Anthony's '07 | 2006 Suffolk Coaches Boys XC Results | 2006 |
| 60 | 16:56.58 | Mike WattsIslip | Islip '14 | Section XI Cross Country County Championships | 2013 |
| 61 | 16:57.16 | Jonathan LauerSachem North | Sachem North '17 | Section XI Cross Country County Championships | 2014 |
| 62 | 16:57.25 | Wyeth SemoNorthport | Northport '22 | Section XI State Qualifier Meet | 2019 |
| 63 | 16:57.40 | James BurkePort Jefferson | Port Jefferson '15 | Section XI Cross Country County Championships | 2014 |
| 64 | 16:58.1 | Zack WilliamsRocky Point | Rocky Point | Nassau County Coaches Association Cross Country Invitational | 2004 |
| 65 | 16:58.36 | David CabelloSmithtown West | Smithtown West '19 | Section XI State Qualifier Meet | 2018 |
| 66 | 16:59.36 | Nicholas CipollaSmithtown West | Smithtown West '18 | Section XI State Qualifier Meet | 2017 |
| 67 | 16:59.56 | Thomas CirritoMiller Place | Miller Place '20 | Section XI State Qualifier Meet | 2018 |
| 68 | 17:00.0 | Brian MorrisSachem | Sachem '04 | Nassau County Coaches Association Cross Country Invitational | 2002 |
| 69 | 17:00.40 | Aiden SmythWalt Whitman | Walt Whitman '18 | Section XI State Qualifier Meet | 2017 |
| 70 | 17:00.54 | Brendan ConnellSmithtown East | Smithtown East '09 | Jim Smith Invitational | 2008 |
| 71 | 17:00.77 | Luciano FioreBay Shore | Bay Shore '15 | Section XI Cross Country County Championships | 2014 |
| 72 | 17:01.22 | James EsernioWard Melville | Ward Melville '15 | Section XI Cross Country County Championships | 2014 |
| 73 | 17:01.49 | Eric ZulkofskeWard Melville | Ward Melville '18 | Section XI State Qualifier Meet | 2017 |
| 74 | 17:02.19 | Chad MaierWalt Whitman | Walt Whitman '15 | Section XI Cross Country County Championships | 2014 |
| 75 | 17:02.28 | Timothy MonahanConnetquot | Connetquot '16 | Section XI Cross Country County Championships | 2013 |
| 76 | 17:03.19 | Matt SantoroSayville | Sayville '07 | 2006 Section XI SQ Boys XC Results | |
| 77 | 17:03.33 | Shawn BofingerBayport-Blue Point | Bayport-Blue Point '15 | Section XI Cross Country County Championships | 2014 |
| 78 | 17:05.12 | Jamison SherrettsNorth Babylon | North Babylon '14 | Section XI Cross Country County Championships | 2013 |
| 79 | 17:05.26 | Casey BarrettSayville | Sayville '07 | 2006 Section XI SQ Boys XC Results | |
| 80 | 17:05.69 | Jeremy MiekleyMiller Place | Miller Place '14 | Section XI Cross Country County Championships | 2013 |
| 81 | 17:05.79 | Kal LewisShelter Island | Shelter Island '20 | Section XI State Qualifier Meet | 2017 |
| 82 | 17:05.90 | Andrew MillerNorthport | Northport '06 | Section XI Cross Country | 2004 |
| 83 | 17:06.99 | Dan O'ConnorNorthport | Northport '18 | Section XI State Qualifier Meet | 2017 |
| 84 | 17:07.02 | Sean RyanNorthport | Northport '19 | Section XI State Qualifier Meet | 2018 |
| 85 | 17:07.1 | Patrick O'DonnellSachem East | Sachem East '07 | Nassau County Coaches Association Cross Country Invitational | 2004 |
| 86 | 17:07.30 | Charlie TheissWard Melville | Ward Melville '15 | Section XI Cross Country County Championships | 2014 |
| 87 | 17:07.55 | Chris NienburgWard Melville | Ward Melville '19 | Section XI State Qualifier Meet | 2017 |
| 88 | 17:08.12 | Kyle KellyWest Islip | West Islip '16 | Section XI Cross Country County Championships | 2014 |
| 89 | 17:08.12 | Skyler LattucaLongwood | Longwood '17 | Section XI Cross Country County Championships | 2014 |
| 90 | 17:08.50 | Jason SantosSmithtown West | Smithtown West '09 | Jim Smith Invitational | 2008 |
| 91 | 17:08.58 | Christian BerberichSachem East | Sachem East '20 | Section XI State Qualifier Meet | 2019 |
| 92 | 17:09.27 | Daniel BlockSachem North | Sachem North '15 | Section XI Cross Country County Championships | 2014 |
| 93 | 17:09.66 | Erik EngstromEast Hampton | East Hampton '16 | Section XI Cross Country County Championships | 2014 |
| 94 | 17:09.92 | Vincent TripiSachem North | Sachem North '19 | Section XI State Qualifier Meet | 2018 |
| 95 | 17:10.08 | Will LappConnetquot | Connetquot '07 | 2006 Section XI SQ Boys XC Results | |
| 96 | 17:10.34 | Nick PandolfoSachem East | Sachem East '16 | Section XI Cross Country County Championships | 2014 |
| 97 | 17:10.88 | Luke GliganicBay Shore | Bay Shore | SBU XC06 Boys Results | 2006 |
| 98 | 17:11.33 | Dylan JungSayville | Sayville '07 | 2006 Section XI SQ Boys XC Results | |
| 99 | 17:11.36 | Matt TemmeLongwood | Longwood '07 | 2006 Section XI SQ Boys XC Results | |
| 100 | 17:11.69 | Dylan ConwayHauppauge | Hauppauge '08 | 2006 Section XI SQ Boys XC Results | |
