| 1 | 12:53.67 | Brendan MartinSmithtown West | Smithtown West '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 2 | 12:53.97 | Quinn RasemanWard Melville | Ward Melville '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 3 | 13:01.25 | Kenneth WalshakSt. Anthony's | St. Anthony's '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 4 | 13:09.93 | Robert FlemingSt. Anthony's | St. Anthony's '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 5 | 13:11.78 | Patrick TuckerSt. Anthony's | St. Anthony's '15 | NSCHSAA Sophomore Championships | 2012 |
| 6 | 13:17.96 | Patrick MurphySt. Anthony's | St. Anthony's '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 7 | 13:19.16 | Thomas ShoulerSt. Anthony's | St. Anthony's '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 8 | 13:20.74 | Matthew PayampsSt. Anthony's | St. Anthony's '19 | NSCHSAA Sophomore Championships | 2016 |
| 9 | 13:22.75 | Joseph TuckerSt. Anthony's | St. Anthony's '15 | NSCHSAA Sophomore Championships | 2012 |
| 10 | 13:22.86 | Brendan DearieSt. Anthony's | St. Anthony's '19 | NSCHSAA Sophomore Championships | 2016 |
| 11 | 13:25.86 | Thomas FlynnSt. Anthony's | St. Anthony's '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 12 | 13:26.69 | Zach WilliamsonRocky Point | Rocky Point '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 13 | 13:27.22 | Kevin GwinnSt. Anthony's | St. Anthony's '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 14 | 13:28.67 | Stephen RussSt. Anthony's | St. Anthony's '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 15 | 13:31.08 | Brant CavagnaroBay Shore | Bay Shore '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 16 | 13:32.01 | Michael McCRISTALLHauppauge | Hauppauge '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 17 | 13:32.93 | McMullin JohnSt. Anthony's | St. Anthony's '14 | NSCHSAA Sophomore Championships | 2011 |
| 18 | 13:33.16 | Daniel FrostSmithtown West | Smithtown West '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 19 | 13:35.28 | Barry FranklinLongwood | Longwood '08 | Saint Anthony's Cross Country Invitational | 2005 |
| 20 | 13:36.52 | Timothy KeeganSt. Anthony's | St. Anthony's '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 21 | 13:37.58 | Tyler WolfeHuntington | Huntington '14 | NSCHSAA Sophomore Championships | 2011 |
| 22 | 13:40.56 | Donato GeraciLongwood | Longwood '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 23 | 13:40.86 | Matt TemmeLongwood | Longwood '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 24 | 13:41.43 | Casey BarrettSayville | Sayville '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 25 | 13:42.16 | Jeffrey MarroneSt. Anthony's | St. Anthony's '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 26 | 13:44.52 | Nicholas JonesSt. Anthony's | St. Anthony's '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 27 | 13:45.46 | Matthew ClarkeSt. Anthony's | St. Anthony's '15 | NSCHSAA Sophomore Championships | 2012 |
| 28 | 13:46.53 | Paolo FioreSt. John the Baptist | St. John the Baptist '13 | NSCHSAA Sophomore Championships | 2010 |
| 29 | 13:47.01 | Dylan ConwayHauppauge | Hauppauge '08 | Saint Anthony's Cross Country Invitational | 2005 |
| 30 | 13:47.71 | Robert DohertySt. Anthony's | St. Anthony's '21 | NSCHSAA Sophomore Championships | 2018 |
| 31 | 13:48.04 | Nicohlas CollazosSouthampton | Southampton '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 32 | 13:48.05 | Pat BoerjesSt. John the Baptist | St. John the Baptist '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 33 | 13:49.76 | Jake HenslerSt. Anthony's | St. Anthony's '13 | NSCHSAA Sophomore Championships | 2010 |
| 34 | 13:49.77 | Patrick KainSt. John the Baptist | St. John the Baptist '18 | NSCHSAA Sophomore Championships | 2015 |
| 35 | 13:50.03 | Patrick FiorilloSt. John the Baptist | St. John the Baptist '20 | NSCHSAA Sophomore Championships | 2017 |
| 36 | 13:50.61 | Matt ZamparielloSt. John the Baptist | St. John the Baptist '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 37 | 13:50.73 | Andrew MillerNorthport | Northport '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 38 | 13:51.09 | Nicholas BrennanSt. Anthony's | St. Anthony's '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 39 | 13:51.51 | Steve FergusonSt. John the Baptist | St. John the Baptist '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 40 | 13:51.82 | William HenflingSt. Anthony's | St. Anthony's '14 | NSCHSAA Sophomore Championships | 2011 |
| 41 | 13:51.86 | Jim BoscoSt. John the Baptist | St. John the Baptist '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 42 | 13:53.05 | Matthew TaddeoSt. Anthony's | St. Anthony's '13 | NSCHSAA Sophomore Championships | 2010 |
| 43 | 13:54.53 | Robert TasseySt. Anthony's | St. Anthony's '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 44 | 13:55.34 | Brian SmithSt. Anthony's | St. Anthony's '12 | NSCHSAA Sophomore Championships | 2009 |
| 45 | 13:56.23 | Austin ConeysHarborfields | Harborfields '12 | Saint Anthony's Cross Country Invitational | 2009 |
| 46 | 13:56.46 | Thomas LouroSt. Anthony's | St. Anthony's '14 | NSCHSAA Sophomore Championships | 2011 |
| 47 | 13:56.74 | Matt MurphyConnetquot | Connetquot '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 48 | 13:57.81 | Joseph KeaneSt. Anthony's | St. Anthony's '15 | NSCHSAA Sophomore Championships | 2012 |
| 49 | 13:58.26 | Patrick SlutterHarborfields | Harborfields '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 50 | 13:59.25 | Brian KreiderSt. Anthony's | St. Anthony's '14 | NSCHSAA Sophomore Championships | 2011 |
| 51 | 14:01.12 | Matt SmithBellport | Bellport '08 | Saint Anthony's Cross Country Invitational | 2005 |
| 52 | 14:01.19 | Amani MorrellSt. Anthony's | St. Anthony's '18 | NSCHSAA Sophomore Championships | 2015 |
| 53 | 14:01.83 | Kevin TigheSt. John the Baptist | St. John the Baptist '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 54 | 14:02.88 | Sean FitzgeraldSt. Anthony's | St. Anthony's '13 | NSCHSAA Sophomore Championships | 2010 |
| 55 | 14:04.38 | Dillion JungSayville | Sayville '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 56 | 14:04.92 | Tim SeebergerSt. John the Baptist | St. John the Baptist '15 | NSCHSAA Sophomore Championships | 2012 |
| 57 | 14:05.72 | James JohnstonLongwood | Longwood '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 58 | 14:06.13 | Jesse ThompsonBay Shore | Bay Shore '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 59 | 14:06.86 | Fernando SanchezSt. John the Baptist | St. John the Baptist '21 | NSCHSAA Sophomore Championships | 2018 |
| 60 | 14:06.98 | Aidan HealySt. John the Baptist | St. John the Baptist '18 | NSCHSAA Sophomore Championships | 2015 |
| 61 | 14:07.69 | Danny HarrisSt. John the Baptist | St. John the Baptist '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 62 | 14:07.70 | Andrew AraujoBay Shore | Bay Shore '08 | Saint Anthony's Cross Country Invitational | 2005 |
| 63 | 14:08.06 | Matthew FortinoSt. Anthony's | St. Anthony's '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 64 | 14:08.37 | Matt SantoroSayville | Sayville '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 65 | 14:09.10 | Brandon CamenzuliSt. John the Baptist | St. John the Baptist '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 66 | 14:09.26 | Andrew SanchezNorthport | Northport '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 67 | 14:09.66 | Christian RojasSt. John the Baptist | St. John the Baptist '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 68 | 14:10.70 | Jeff LesserHauppauge | Hauppauge '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 69 | 14:11.85 | Michael MauroBay Shore | Bay Shore '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 70 | 14:11.86 | Frank SegretoSt. Anthony's | St. Anthony's '12 | NSCHSAA Sophomore Championships | 2009 |
| 71 | 14:12.84 | Cody CorcoranBay Shore | Bay Shore '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 72 | 14:13.08 | Ben HoganBay Shore | Bay Shore '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 73 | 14:13.59 | James StavdalLongwood | Longwood '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 74 | 14:14.55 | John O'ConnellSt. John the Baptist | St. John the Baptist '20 | NSCHSAA Sophomore Championships | 2017 |
| 75 | 14:14.83 | Bryan ReillySt. John the Baptist | St. John the Baptist '14 | NSCHSAA Sophomore Championships | 2011 |
| 76 | 14:15.00 | Alex BoccardHarborfields | Harborfields '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 77 | 14:15.27 | Kevin SolarSt. Anthony's | St. Anthony's '14 | NSCHSAA Sophomore Championships | 2011 |
| 78 | 14:15.51 | Kieran O'SheaSt. Anthony's | St. Anthony's '14 | NSCHSAA Sophomore Championships | 2011 |
| 79 | 14:15.61 | Marc SaracinoSt. Anthony's | St. Anthony's '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 80 | 14:16.10 | Sean FergusonSt. John the Baptist | St. John the Baptist '12 | NSCHSAA Sophomore Championships | 2009 |
| 81 | 14:16.97 | Michael Barbaro-BarnettSt. Anthony's | St. Anthony's '19 | NSCHSAA Sophomore Championships | 2016 |
| 82 | 14:17.70 | Thomas RouletteSt. John the Baptist | St. John the Baptist '18 | NSCHSAA Sophomore Championships | 2015 |
| 83 | 14:18.14 | Hunter VierlingSt. Anthony's | St. Anthony's '19 | NSCHSAA Sophomore Championships | 2016 |
| 84 | 14:18.23 | Ben HaffnerNorthport | Northport '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 85 | 14:19.24 | Joe SantosusSmithtown East | Smithtown East '07 | Saint Anthony's Cross Country Invitational | 2005 |
| 86 | 14:19.56 | Robert CherkisSt. Anthony's | St. Anthony's '09 | Saint Anthony's Cross Country Invitational | 2005 |
| 87 | 14:20.61 | Nick CirasoleSt. John the Baptist | St. John the Baptist '18 | NSCHSAA Sophomore Championships | 2015 |
| 88 | 14:21.17 | Ryan BoydBayport-Blue Point | Bayport-Blue Point '08 | Saint Anthony's Cross Country Invitational | 2005 |
| 89 | 14:21.43 | Brandon KeanySt. Anthony's | St. Anthony's '10 | Saint Anthony's Cross Country Invitational | 2009 |
| 90 | 14:21.73 | Kyle McCormackSt. John the Baptist | St. John the Baptist '18 | NSCHSAA Sophomore Championships | 2015 |
| 91 | 14:21.96 | Christopher ReganSt. Anthony's | St. Anthony's '13 | NSCHSAA Sophomore Championships | 2010 |
| 92 | 14:22.28 | Ryan GilleenyWard Melville | Ward Melville '11 | Saint Anthony's Cross Country Invitational | 2009 |
| 93 | 14:22.70 | Ryan BennisSt. John the Baptist | St. John the Baptist '14 | NSCHSAA Sophomore Championships | 2011 |
| 94 | 14:23.27 | Thomas DilibertoSt. Anthony's | St. Anthony's '12 | NSCHSAA Sophomore Championships | 2009 |
| 95 | 14:23.85 | Charlie StenzingerSayville | Sayville '06 | Saint Anthony's Cross Country Invitational | 2005 |
| 96 | 14:24.72 | Aaron ZigrosserSt. John the Baptist | St. John the Baptist '15 | NSCHSAA Sophomore Championships | 2012 |
| 97 | 14:24.94 | Brian HealySt. John the Baptist | St. John the Baptist '20 | NSCHSAA Sophomore Championships | 2017 |
| 98 | 14:25.20 | Luke ConnollySt. Anthony's | St. Anthony's '21 | NSCHSAA Sophomore Championships | 2018 |
| 99 | 14:25.23 | William MadreyIslip | Islip '08 | Saint Anthony's Cross Country Invitational | 2005 |
| 100 | 14:26.49 | William IsenbergSt. Anthony's | St. Anthony's '13 | NSCHSAA Sophomore Championships | 2010 |
