| 1 | 16:23.84 | Thomas SlatteryChaminade | Chaminade '14 | NSCHSAA League Championships | 2013 |
| 2 | 16:24.94 | Kevin McDermottChaminade | Chaminade '05 | CHSAA XC League Championships | 2004 |
| 3 | 16:25.35 | Sean KellyChaminade | Chaminade '14 | NSCHSAA League Championships | 2013 |
| 4 | 16:34.04 | Jack CurranCalhoun | Calhoun '13 | Suffolk Coaches Invitational | 2012 |
| 5 | 16:34.44 | Thomas AwadChaminade | Chaminade '12 | NSCHSAA League Championships | 2011 |
| 6 | 16:35.33 | Ryan CooneyMassapequa | Massapequa '13 | Saint Anthony's Cross Country Invitational | 2012 |
| 7 | 16:39.50 | Gunnar NolanChaminade | Chaminade '15 | NSCHSAA League Championships | 2013 |
| 8 | 16:44.74 | Daniel SiegelGreat Neck South | Great Neck South '11 | Bob Pratt Cross Country Invitational | 2010 |
| 9 | 16:45.56 | Jack RosencransNorth Shore | North Shore '19 | Saint Anthony's Cross Country Invitational | 2018 |
| 10 | 16:47.07 | Joseph FerencikChaminade | Chaminade '12 | NSCHSAA League Championships | 2011 |
| 11 | 16:47.94 | Jason LinzerSeaford | Seaford '20 | Saint Anthony's Cross Country Invitational | 2018 |
| 12 | 16:49.83 | Owen SkeeteWestbury | Westbury '11 | Suffolk Officials XC Invitational | 2010 |
| 13 | 16:53.19 | Elias PlataniasCalhoun | Calhoun '16 | Suffolk Coaches Invitational | 2015 |
| 14 | 16:56.94 | Stephen BourguetManhasset | Manhasset '13 | Bob Pratt Cross Country Invitational | 2012 |
| 15 | 16:59.49 | Brandon AbasoloLong Beach | Long Beach '09 | Bob Pratt Cross Country Invitational | 2008 |
| 16 | 17:01.27 | Andrew MorraGarden City | Garden City '13 | Saint Anthony's Cross Country Invitational | 2012 |
| 17 | 17:02.15 | Sidharth KakkarPort Washington | Port Washington '13 | Saint Anthony's Cross Country Invitational | 2011 |
| 18 | 17:03.21 | William SlatteryChaminade | Chaminade '11 | NSCHSAA League Championships | 2010 |
| 19 | 17:03.58 | Arquimedes Dela CruzWantagh | Wantagh '09 | Bob Pratt Cross Country Invitational | 2008 |
| 20 | 17:03.98 | Christian CiciliaValley Stream North | Valley Stream North '20 | Suffolk Officials XC Invitational | 2018 |
| 21 | 17:04.54 | Tim JosephsGarden City | Garden City '15 | Suffolk Coaches Invitational | 2014 |
| 22 | 17:04.87 | Zachary TonerCalhoun | Calhoun '13 | Suffolk Coaches Invitational | 2012 |
| 23 | 17:05.36 | Taylor TitcombPort Washington | Port Washington '12 | Saint Anthony's Cross Country Invitational | 2011 |
| 24 | 17:05.42 | David LoziponeKellenberg | Kellenberg '18 | NSCHSAA League Championships | 2017 |
| 25 | 17:05.73 | Charlie MorrisManhasset | Manhasset '12 | Saint Anthony's Cross Country Invitational | 2011 |
| 26 | 17:05.86 | Alex TosiOyster Bay | Oyster Bay '16 | Saint Anthony's Cross Country Invitational | 2015 |
| 27 | 17:06.49 | Patrick ConklinChaminade | Chaminade '18 | NSCHSAA League Championships | 2016 |
| 28 | 17:06.99 | Andrew CoelhoWantagh | Wantagh '09 | Bob Pratt Cross Country Invitational | 2008 |
| 29 | 17:07.41 | Matthew WalshChaminade | Chaminade '13 | NSCHSAA League Championships | 2012 |
| 30 | 17:09.96 | Brendan McGannChaminade | Chaminade '06 | CHSAA XC League Championships | 2004 |
| 31 | 17:10.08 | Christian AltamuraMacArthur | MacArthur '09 | Bob Pratt Cross Country Invitational | 2008 |
| 32 | 17:11.37 | Andrew ValenskiMassapequa | Massapequa '11 | Bob Pratt Cross Country Invitational | 2008 |
| 33 | 17:11.42 | Connor FitzpatrickChaminade | Chaminade '17 | NSCHSAA League Championships | 2016 |
| 34 | 17:11.74 | Marco BertolottiPort Washington | Port Washington '10 | Suffolk Officials XC Invitational | 2009 |
| 35 | 17:11.86 | Ryan McDermottChaminade | Chaminade '07 | CHSAA XC League Championships | 2004 |
| 36 | 17:12.64 | James AgatiKellenberg | Kellenberg '11 | NSCHSAA League Championships | 2010 |
| 37 | 17:13.36 | Matthew WoopChaminade | Chaminade '11 | NSCHSAA League Championships | 2010 |
| 38 | 17:16.08 | Peter KirgisPort Washington | Port Washington '16 | Suffolk Coaches Invitational | 2014 |
| 39 | 17:16.47 | Joseph MillerSeaford | Seaford '14 | Saint Anthony's Cross Country Invitational | 2013 |
| 40 | 17:16.65 | Jordan AshleyJFK Bellmore | JFK Bellmore '09 | Bob Pratt Cross Country Invitational | 2008 |
| 41 | 17:18.28 | Christopher PerilloMepham | Mepham '16 | Suffolk Coaches Invitational | 2014 |
| 42 | 17:18.78 | Landi ChristopherCalhoun | Calhoun '13 | Suffolk Coaches Invitational | 2012 |
| 43 | 17:19.90 | Brendan McGrathChaminade | Chaminade '19 | NSCHSAA League Championships | 2018 |
| 44 | 17:20.15 | Sean ButlerChaminade | Chaminade '15 | NSCHSAA League Championships | 2014 |
| 45 | 17:20.26 | Aaron Siff-ScherrPort Washington | Port Washington '17 | Bob Pratt Boys Results | |
| 46 | 17:20.59 | Gregory HoffmanChaminade | Chaminade '05 | CHSAA XC League Championships | 2004 |
| 47 | 17:20.67 | Chris TaylorValley Stream South | Valley Stream South '06 | Bob Pratt Cross Country Invitational | 2008 |
| 48 | 17:20.94 | Aidan CaggianoManhasset | Manhasset '18 | Bob Pratt Boys Results | |
| 49 | 17:21.25 | Steven HoffmanKellenberg | Kellenberg '17 | NSCHSAA League Championships | 2016 |
| 50 | 17:21.52 | Timothy EulerEast Meadow | East Meadow '17 | Jim Smith Invitational | 2016 |
| 51 | 17:22.06 | Nick FilippazzoWantagh | Wantagh '10 | Bob Pratt Cross Country Invitational | 2008 |
| 52 | 17:22.40 | Timothy CourtsManhasset | Manhasset '16 | Suffolk Coaches Invitational | 2015 |
| 53 | 17:22.75 | Joshua MichelKellenberg | Kellenberg '19 | NSCHSAA League Championships | 2016 |
| 54 | 17:23.98 | Thomas HayesChaminade | Chaminade '14 | NSCHSAA League Championships | 2013 |
| 55 | 17:24.82 | David BransfieldKellenberg | Kellenberg '11 | NSCHSAA League Championships | 2010 |
| 56 | 17:26.15 | Eric RatnerClarke | Clarke '12 | Jim Smith Invitational | 2011 |
| 57 | 17:27.40 | Kyle SmithMassapequa | Massapequa '13 | Bob Pratt Cross Country Invitational | 2012 |
| 58 | 17:27.54 | Raul McGeeKellenberg | Kellenberg '12 | NSCHSAA League Championships | 2011 |
| 59 | 17:28.03 | Randall TurnerKellenberg | Kellenberg '13 | NSCHSAA League Championships | 2012 |
| 60 | 17:28.21 | Ryan RosmarinFriends Academy | Friends Academy '10 | Suffolk Officials XC Invitational | 2009 |
| 61 | 17:28.41 | Brian SchmidtKellenberg | Kellenberg '07 | CHSAA XC League Championships | 2004 |
| 62 | 17:29.15 | Ryan CurranCalhoun | Calhoun '16 | Suffolk Coaches Invitational | 2013 |
| 63 | 17:29.51 | Depinto RyanSyosset | Syosset '14 | Jim Smith Invitational | 2011 |
| 64 | 17:30.25 | John WeedValley Stream Central | Valley Stream Central '15 | Bob Pratt Cross Country Invitational | 2014 |
| 65 | 17:30.37 | Thomas ClarkWantagh | Wantagh '09 | Bob Pratt Cross Country Invitational | 2008 |
| 66 | 17:31.22 | John AneserChaminade | Chaminade '14 | NSCHSAA League Championships | 2013 |
| 67 | 17:32.06 | Aidan SmithMassapequa | Massapequa '16 | Bob Pratt Cross Country Invitational | 2015 |
| 68 | 17:32.67 | Glenn LostrittoFriends Acad | Friends Acad '15 | Suffolk Officials XC Invitational | 2012 |
| 69 | 17:33.00 | Daniel ReillyWantagh | Wantagh '12 | Saint Anthony's Cross Country Invitational | 2011 |
| 70 | 17:33.54 | Conor McNamaraChaminade | Chaminade '06 | CHSAA XC League Championships | 2004 |
| 71 | 17:34.07 | Jake CatalanoValley Stream North | Valley Stream North '16 | Saint Anthony's Cross Country Invitational | 2014 |
| 72 | 17:34.35 | John CyprusManhasset | Manhasset '18 | Bob Pratt Cross Country Invitational | 2017 |
| 73 | 17:35.49 | Steven ForteMepham | Mepham '14 | Saint Anthony's Cross Country Invitational | 2012 |
| 74 | 17:36.86 | Raymond McCuskerChaminade | Chaminade '16 | NSCHSAA League Championships | 2015 |
| 75 | 17:37.35 | James MoehringerMepham | Mepham '17 | Saint Anthony's Cross Country Invitational | 2016 |
| 76 | 17:37.71 | Christopher CourtsManhasset | Manhasset '19 | Suffolk Coaches Invitational | 2018 |
| 77 | 17:37.77 | Forte StevenMepham | Mepham '14 | Saint Anthony's Cross Country Invitational | 2013 |
| 78 | 17:38.07 | Scott PourshalchiRoslyn | Roslyn '15 | Saint Anthony's Cross Country Invitational | 2013 |
| 79 | 17:38.50 | Alex CowenGreat Neck South | Great Neck South '14 | Suffolk Officials XC Invitational | 2012 |
| 80 | 17:40.46 | Charles SkidmoreMepham | Mepham '15 | Jim Smith Invitational | 2014 |
| 81 | 17:40.88 | Jordan HurtPort Washington | Port Washington '17 | Bob Pratt Boys Results | |
| 82 | 17:40.90 | Christopher LoumeauChaminade | Chaminade '17 | NSCHSAA League Championships | 2016 |
| 83 | 17:42.76 | Nick TardugnoOyster Bay | Oyster Bay '21 | 49th Saint Anthony's Cross Country Invitational | 2019 |
| 84 | 17:43.88 | Francis O'BrienKellenberg | Kellenberg '18 | NSCHSAA League Championships | 2017 |
| 85 | 17:44.89 | Christopher StrzeliChaminade | Chaminade '17 | NSCHSAA League Championships | 2015 |
| 86 | 17:44.99 | Andrew AdelhardtPort Washington | Port Washington '16 | Suffolk Officials XC Invitational | 2015 |
| 87 | 17:45.13 | Andrew McAwardChaminade | Chaminade '11 | NSCHSAA League Championships | 2010 |
| 88 | 17:45.49 | Michael DarnellWantagh | Wantagh '12 | Saint Anthony's Cross Country Invitational | 2011 |
| 89 | 17:45.66 | Peter WilkValley Stream North | Valley Stream North '15 | Saint Anthony's Cross Country Invitational | 2014 |
| 90 | 17:45.83 | David DurdallerHewlett | Hewlett '20 | Suffolk Officials XC Invitational | 2018 |
| 91 | 17:45.95 | Christopher LoveKellenberg | Kellenberg '17 | NSCHSAA League Championships | 2016 |
| 92 | 17:46.21 | Conor HampelChaminade | Chaminade '05 | CHSAA XC League Championships | 2004 |
| 93 | 17:46.86 | Thomas BurfeindNorth Shore | North Shore '21 | Saint Anthony's Cross Country Invitational | 2018 |
| 94 | 17:47.05 | Matt MonohanFloral Park Memorial | Floral Park Memorial '17 | Bob Pratt Boys Results | |
| 95 | 17:47.11 | Daniel ValentiGarden City | Garden City '17 | Suffolk Coaches Invitational | 2015 |
| 96 | 17:49.07 | Collin SullivanNorth Shore | North Shore '18 | Saint Anthony's Cross Country Invitational | 2017 |
| 97 | 17:49.09 | Daniel GrahamHoly Trinity | Holy Trinity '15 | NSCHSAA League Championships | 2013 |
| 98 | 17:49.87 | Nicolas SapountzisPort Washington | Port Washington '13 | Bob Pratt Cross Country Invitational | 2012 |
| 99 | 17:49.99 | Bryan VillafuerteEast Meadow | East Meadow '19 | Saint Anthony's Cross Country Invitational | 2018 |
| 100 | 17:49.99 | Matt MonahanFloral Park Memorial | Floral Park Memorial '17 | Suffolk Coaches Invitational | 2016 |
