| 1 | 7:55.55 | Brendan GallagherSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 2 | 8:01.10 | Matthew NockSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 3 | 8:19.37 | Pat CollinsBayport-Blue Point | Bayport-Blue Point '12 | St. Anthony's Invitational | 2008 |
| 4 | 8:20.16 | Thomas DilibertoSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 5 | 8:24.70 | Kevin KreiderSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 6 | 8:28.52 | Liam MurphyBellport | Bellport '20 | NSCHSAA Varsity Champs | 2009 |
| 7 | 8:30.24 | Daniel MeehanSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 8 | 8:30.75 | Robert FerraraSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 9 | 8:33.30 | Gerard BenfieldSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 10 | 8:34.77 | Jamie CalabrettaSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 11 | 8:39.94 | Douglas AtenieseSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 12 | 8:39.94 | Keith VitaSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 13 | 8:42.18 | Brian SmithSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 14 | 8:44.86 | Frank SegretoSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 15 | 8:46.84 | Matthew PluhowskiSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 16 | 8:54.75 | Eric MacalusoSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 17 | 8:58.76 | Thomas HallSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 18 | 9:08.42 | Philip IervolinoSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 19 | 9:14.04 | Gene KumSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 20 | 9:15.48 | Kyle ButlerSt. John the Baptist | St. John the Baptist '13 | NSCHSAA Varsity Champs | 2009 |
| 21 | 9:16.82 | Thomas DuPlessisSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 22 | 9:19.28 | Thomas GormanSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 23 | 9:20.59 | Frank Segreto ASt. Anthony's | St. Anthony's | CHSAA Frosh/Soph Championships | 2008 |
| 24 | 9:26.62 | Salvatore GiulianoSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 25 | 9:32.01 | Joshua AschSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 26 | 9:39.82 | Christian PetersenSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 27 | 9:40.00 | Matt McDermottSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 28 | 9:40.57 | Kevin KruseSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 29 | 9:40.93 | John BurkeSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 30 | 9:44.39 | Gerard NicosiaSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 31 | 9:50.87 | Dominic NastasiSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 32 | 9:52.26 | Ryan SheppardSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 33 | 9:52.74 | Andrew MelonSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 34 | 9:55.64 | Austin SedaSt. Anthony's | St. Anthony's '12 | CHSAA Frosh/Soph Championships | 2008 |
| 35 | 9:56.31 | Michael FalconeSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 36 | 10:00.11 | Andrew SeamanSt. John the Baptist | St. John the Baptist '13 | NSCHSAA Varsity Champs | 2009 |
| 37 | 10:06.63 | Christian EybergenSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 38 | 10:08.81 | Kevin BaistSt. John the Baptist | St. John the Baptist '13 | NSCHSAA Varsity Champs | 2009 |
| 39 | 10:14.97 | Joshua BrownSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 40 | 10:17.85 | Frank VulpiSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 41 | 10:19.12 | Michael RavellaSt. Anthony's | St. Anthony's '12 | CHSAA Frosh/Soph Championships | 2008 |
| 42 | 10:26.95 | Peter ScalfaniSt. Joseph by the Sea | St. Joseph by the Sea '12 | CHSAA Frosh/Soph Championships | 2008 |
| 43 | 10:29.42 | Karlo DinerosSt. John the Baptist | St. John the Baptist '13 | NSCHSAA Varsity Champs | 2009 |
| 44 | 10:37.40 | Alex BoumoussaSt. Joseph by the Sea | St. Joseph by the Sea '12 | CHSAA Frosh/Soph Championships | 2008 |
| 45 | 10:41.79 | Brendan KosubinskySt. Anthony's | St. Anthony's '13 | NSCHSAA Varsity Champs | 2009 |
| 46 | 10:44.75 | Keith UySt. John the Baptist | St. John the Baptist '13 | NSCHSAA Varsity Champs | 2009 |
| 47 | 10:49.41 | Matthew GoidellSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 48 | 10:51.67 | Matthew HeffernanCommack | Commack '27 | NSCHSAA Varsity Champs | 2009 |
| 49 | 10:56.06 | Nicholas GonzalezSouthampton | Southampton | CHSAA Frosh/Soph Championships | 2008 |
| 50 | 11:13.43 | Tom SheridanSt. Joseph by the Sea | St. Joseph by the Sea '12 | CHSAA Frosh/Soph Championships | 2008 |
| 51 | 11:25.36 | Nick RuggieroSt. Joseph by the Sea | St. Joseph by the Sea '12 | CHSAA Frosh/Soph Championships | 2008 |
| 52 | 11:31.57 | Anthony FischettiSachem East | Sachem East '13 | CHSAA Frosh/Soph Championships | 2008 |
| 53 | 12:14.83 | Jihoon KimSt. Anthony's | St. Anthony's '12 | CHSAA Frosh/Soph Championships | 2008 |
| 54 | 12:17.62 | Nicholas SepulvedaSt. Anthony's | St. Anthony's '12 | St. Anthony's Invitational | 2008 |
| 55 | 13:00.13 | Pat McCarthyEast Islip | East Islip '05 | CHSAA Frosh/Soph Championships | 2008 |
| 56 | 13:08.35 | Patrick O'HaraSt. John the Baptist | St. John the Baptist '16 | NSCHSAA Varsity Champs | 2009 |
| 57 | 13:56.81 | Chug KevinSt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
| 58 | 14:00.15 | Ryan O'GradeySt. John the Baptist | St. John the Baptist '12 | St. Anthony's Invitational | 2008 |
