| 1 | 7:58.21 | Tyler WolfeHuntington | Huntington '14 | Saint Anthony's Cross Country Invitational | 2009 |
| 2 | 8:05.50 | Paolo FioreSt. John the Baptist | St. John the Baptist '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 3 | 8:07.54 | Christian WelchWard Melville | Ward Melville '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 4 | 8:19.64 | Chris RiveraSt. John the Baptist | St. John the Baptist '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 5 | 8:47.96 | Michael FrawleySt. John the Baptist | St. John the Baptist '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 6 | 8:52.75 | Kyle BrennanHarborfields | Harborfields '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 7 | 8:53.45 | Alex StoneHarborfields | Harborfields '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 8 | 9:00.75 | Thomas BoisclairHuntington | Huntington '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 9 | 9:09.77 | Robert ChallenorSt. John the Baptist | St. John the Baptist '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 10 | 9:10.26 | Andrew AttivisimoHarborfields | Harborfields '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 11 | 9:17.22 | Jimmy HamiltonSt. John the Baptist | St. John the Baptist '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 12 | 9:18.61 | Eric LiHarborfields | Harborfields '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 13 | 9:20.11 | Eric HochwaldHarborfields | Harborfields '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 14 | 9:22.77 | Ryan DyckesHuntington | Huntington '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 15 | 9:33.93 | Dylan SealsHarborfields | Harborfields '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 16 | 9:38.08 | Kyle ButlerSt. John the Baptist | St. John the Baptist '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 17 | 9:38.81 | Keaton LaubSouthampton | Southampton '14 | Saint Anthony's Cross Country Invitational | 2009 |
| 18 | 9:45.96 | James KimHarborfields | Harborfields '13 | Saint Anthony's Cross Country Invitational | 2009 |
| 19 | 15:56.30 | Mike BraniganNorthport | Northport '15 | Section XI Division XC Championships | 2012 |
| 20 | 15:57.10 | Ryan UdvadiaShoreham-Wading River | Shoreham-Wading River '14 | Section XI Division XC Championships | 2012 |
| 21 | 16:04.10 | Michael DamatoWalt Whitman | Walt Whitman '13 | Section XI Division XC Championships | 2012 |
| 22 | 16:04.45 | Jonathan LauerSachem North | Sachem North '17 | Section XI Boys Division XC Championships | 2016 |
| 23 | 16:06.25 | Bobby AndrewsShoreham-Wading River | Shoreham-Wading River '09 | Section XI Division Championships | 2008 |
| 24 | 16:08.30 | Kris MoranNorth Babylon | North Babylon '13 | Section XI Division XC Championships | 2012 |
| 25 | 16:09.40 | Zachary CammerWalt Whitman | Walt Whitman '13 | Section XI Division XC Championships | 2012 |
| 26 | 16:09.40 | Christopher TibbettsSachem North | Sachem North '17 | Section XI State Qualifier Meet | 2016 |
| 27 | 16:11.10 | Tim McGowanNorthport | Northport '14 | Section XI Division XC Championships | 2012 |
| 28 | 16:11.75 | Quinn RasemanWard Melville | Ward Melville '10 | Section XI Division Championships | 2008 |
| 29 | 16:15.00 | James DickinsonNorthport | Northport '13 | Section XI Division XC Championships | 2012 |
| 30 | 16:17.60 | Ryan ColabellaHauppauge | Hauppauge '12 | Section XI Division Championships | 2011 |
| 31 | 16:18.00 | James VallarWalt Whitman | Walt Whitman '13 | Section XI Division XC Championships | 2012 |
| 32 | 16:19.84 | Brendan ConnellSmithtown East | Smithtown East '09 | Section XI Division Championships | 2008 |
| 33 | 16:21.24 | Jason SantosSmithtown West | Smithtown West '09 | Section XI Sectional Championships | 2008 |
| 34 | 16:21.77 | Michael GrabowskiSmithtown West | Smithtown West '17 | Section XI State Qualifier Meet | 2016 |
| 35 | 16:22.48 | Alex SaavedraSachem East | Sachem East '11 | Section XI Sectional Championships | 2008 |
| 36 | 16:22.89 | Isaiah ClaiborneNorthport | Northport '18 | Section XI Boys Division XC Championships | 2017 |
| 37 | 16:24.97 | Christopher TibbetSachem North | Sachem North '17 | Section XI Division XC Championships | 2015 |
| 38 | 16:27.63 | Giovanni SignorettiSmithtown West | Smithtown West '08 | Section XI Division Championships | 2007 |
| 39 | 16:30.30 | Frank FezzaSachem North | Sachem North '09 | Section XI Sectional Championships | 2008 |
| 40 | 16:32.42 | Kal LewisShelter Island | Shelter Island '20 | Section XI Boys Division XC Championships | 2017 |
| 41 | 16:32.82 | Dan O'ConnorNorthport | Northport '18 | Section XI Boys Division XC Championships | 2017 |
| 42 | 16:33.50 | Thomas MeehanEastport-South Manor | Eastport-South Manor '14 | Section XI Division XC Championships | 2012 |
| 43 | 16:33.53 | Chris PohlotShoreham-Wading River | Shoreham-Wading River '11 | Bob Pratt Cross Country Invitational | 2009 |
| 44 | 16:35.90 | Alex KramerNorthport | Northport '13 | Section XI Division XC Championships | 2012 |
| 45 | 16:36.28 | Erik EngstromEast Hampton | East Hampton '16 | Section XI Division XC Championships | 2015 |
| 46 | 16:36.33 | Patrick MurphySt. Anthony's | St. Anthony's '10 | Bob Pratt Cross Country Invitational | 2009 |
| 47 | 16:36.70 | Nick HirdtMiller Place | Miller Place '13 | Section XI Division XC Championships | 2012 |
| 48 | 16:37.50 | Mike WattsIslip | Islip '14 | Section XI Division XC Championships | 2012 |
| 49 | 16:40.34 | Louis SantelliSt. Anthony's | St. Anthony's '14 | Saint Anthony's Cross Country Invitational | 2013 |
| 50 | 16:41.25 | Kyle MerberHalf Hollow Hills West | Half Hollow Hills West '08 | Section XI Division Championships | 2007 |
| 51 | 16:41.52 | Kevin FoleyCommack | Commack '17 | Section XI Division XC Championships | 2015 |
| 52 | 16:42.18 | Jack RyanWesthampton Beach | Westhampton Beach '17 | Section XI State Qualifier Meet | 2016 |
| 53 | 16:42.41 | Jonathon CuomoWilliam Floyd | William Floyd '08 | Section XI Division Championships | 2007 |
| 54 | 16:42.57 | Nicholas CipollaSmithtown West | Smithtown West '18 | Section XI Boys Division XC Championships | 2017 |
| 55 | 16:42.60 | Ryan ScarpelliSachem East | Sachem East '12 | Section XI Division Championships | 2011 |
| 56 | 16:43.00 | John LeeShoreham-Wading River | Shoreham-Wading River '12 | Section XI Division Championships | 2011 |
| 57 | 16:43.23 | Colin AndersonNorthport | Northport '09 | Section XI Division Championships | 2008 |
| 58 | 16:43.30 | Patrick TuckerSt. Anthony's | St. Anthony's '15 | Saint Anthony's Cross Country Invitational | 2013 |
| 59 | 16:43.57 | Sean RyanNorthport | Northport '19 | Section XI Boys Division XC Championships | 2017 |
| 60 | 16:43.95 | Kenneth WalshakSt. Anthony's | St. Anthony's '10 | Bob Pratt Cross Country Invitational | 2009 |
| 61 | 16:44.17 | Ryan ScanlonHarborfields | Harborfields '16 | Section XI Division XC Championships | 2015 |
| 62 | 16:44.60 | Vincent CicaleWard Melville | Ward Melville '13 | Section XI Division XC Championships | 2012 |
| 63 | 16:44.90 | Kyle KellyWest Islip | West Islip '16 | Section XI Division XC Championships | 2015 |
| 64 | 16:45.93 | Skyler LattucaLongwood | Longwood '17 | Section XI Division XC Championships | 2015 |
| 65 | 16:47.13 | Zach KrauseConnetquot | Connetquot '11 | Bob Pratt Cross Country Invitational | 2010 |
| 66 | 16:47.74 | Cabel McCandlessLindenhurst | Lindenhurst '16 | Section XI Division XC Championships | 2015 |
| 67 | 16:47.82 | Nicholas DeFeliceSmithtown West | Smithtown West '19 | Section XI Boys Division XC Championships | 2017 |
| 68 | 16:48.49 | Geoff EngelMiller Place | Miller Place '09 | Section XI Division Championships | 2008 |
| 69 | 16:48.67 | Steven Spreizer JSmithtown | Smithtown '18 | Section XI Boys Division XC Championships | 2017 |
| 70 | 16:48.76 | Evan BloombergNorthport | Northport '09 | Section XI Sectional Championships | 2008 |
| 71 | 16:49.20 | Jeremy MiekleyMiller Place | Miller Place '14 | Section XI Division XC Championships | 2012 |
| 72 | 16:49.54 | Justin AlloneSachem East | Sachem East '18 | Section XI Boys Division XC Championships | 2017 |
| 73 | 16:50.16 | Elijah ClaiborneNorthport | Northport '18 | Section XI Boys Division XC Championships | 2017 |
| 74 | 16:50.22 | Matthew KatzHarborfields | Harborfields '17 | Section XI Boys Division XC Championships | 2016 |
| 75 | 16:50.67 | Kyle WightmanShoreham-Wading River | Shoreham-Wading River '09 | Section XI Division Championships | 2008 |
| 76 | 16:50.79 | Thomas BrockBellport | Bellport '18 | Section XI Boys Division XC Championships | 2016 |
| 77 | 16:51.00 | Aiden SmythWalt Whitman | Walt Whitman '18 | Section XI Boys Division XC Championships | 2017 |
| 78 | 16:51.19 | Chris NienburgWard Melville | Ward Melville '19 | Section XI Boys Division XC Championships | 2017 |
| 79 | 16:51.40 | Liam KellyConnetquot | Connetquot '14 | Section XI Division XC Championships | 2012 |
| 80 | 16:51.65 | Matthew ViscosiWard Melville | Ward Melville '17 | Section XI State Qualifier Meet | 2016 |
| 81 | 16:52.06 | Dominick De MatteoHalf Hollow Hills West | Half Hollow Hills West '09 | Section XI Sectional Championships | 2008 |
| 82 | 16:52.21 | Barry FranklinLongwood | Longwood '08 | Section XI Division Championships | 2007 |
| 83 | 16:54.39 | Carlos SantosPatchogue-Medford | Patchogue-Medford '18 | Section XI Boys Division XC Championships | 2016 |
| 84 | 16:54.59 | Ryan CorbettEastport-South Manor | Eastport-South Manor '17 | Section XI State Qualifier Meet | 2016 |
| 85 | 16:54.82 | David CabelloSmithtown West | Smithtown West '19 | Section XI Boys Division XC Championships | 2017 |
| 86 | 16:55.10 | Adam LaFeminaBayport-Blue Point | Bayport-Blue Point '13 | Section XI Division Championships | 2011 |
| 87 | 16:55.30 | Austin ConeysHarborfields | Harborfields '12 | Section XI Division Championships | 2011 |
| 88 | 16:57.27 | Brandon GuerreraSachem East | Sachem East '17 | Section XI Division XC Championships | 2015 |
| 89 | 16:57.80 | Colin EberhardtSachem North | Sachem North '12 | Section XI Division Championships | 2011 |
| 90 | 16:58.14 | Matthew KnottSmithtown West | Smithtown West '09 | Section XI Division Championships | 2008 |
| 91 | 16:58.42 | Phillip GuntherSayville | Sayville '17 | Section XI State Qualifier Meet | 2016 |
| 92 | 16:58.70 | Robert CalamiaSmithtown East | Smithtown East '12 | Section XI Division Championships | 2011 |
| 93 | 16:58.70 | Jack McGowanNorthport | Northport '14 | Section XI Division XC Championships | 2012 |
| 94 | 17:00.26 | Jared LevyWalt Whitman | Walt Whitman '09 | Section XI Division Championships | 2008 |
| 95 | 17:00.37 | James GladyszShoreham-Wading River | Shoreham-Wading River '09 | Section XI Division Championships | 2008 |
| 96 | 17:00.39 | Tyler MurthaConnetquot | Connetquot '11 | Bob Pratt Cross Country Invitational | 2010 |
| 97 | 17:00.73 | Nick PandolfoSachem East | Sachem East '16 | Section XI Division XC Championships | 2015 |
| 98 | 17:00.77 | Thomas CirritoMiller Place | Miller Place '20 | Section XI Boys Division XC Championships | 2017 |
| 99 | 17:00.80 | Joshua HadityCommack | Commack '15 | Section XI Division XC Championships | 2012 |
| 100 | 17:01.70 | Gary MuranoEastport-South Manor | Eastport-South Manor '13 | Section XI Division XC Championships | 2012 |
