| 1 | 7:23.04 | James BurkePort Jefferson | Port Jefferson '15 | Jim Smith Invitational | 2011 |
| 2 | 7:24.09 | Joseph TuckerSt. Anthony's | St. Anthony's '15 | NSCHSAA League Championships | 2011 |
| 3 | 7:29.36 | Christopher LangerSt. Anthony's | St. Anthony's '16 | Saint Anthony's Cross Country Invitational | 2012 |
| 4 | 7:30.10 | Patrick TuckerSt. Anthony's | St. Anthony's '15 | NSCHSAA League Championships | 2011 |
| 5 | 7:31.76 | Kyle KellyWest Islip | West Islip '16 | Suffolk Coaches XC Invitational | 2011 |
| 6 | 7:34.00 | Ryan MeccaWard Melville | Ward Melville '20 | Suffolk Officials XC Invitational | 2016 |
| 7 | 7:35.15 | Maximus HayniaWesthampton Beach | Westhampton Beach '23 | Jim Smith Invitational | 2019 |
| 8 | 7:38.78 | Kevin HillSt. John the Baptist | St. John the Baptist '08 | CHSAA XC League Championships | 2004 |
| 9 | 7:39.31 | Matthew PayampsSt. Anthony's | St. Anthony's '19 | NSCHSAA League Championships | 2015 |
| 10 | 7:40.11 | Graeme OlsenRiverhead | Riverhead '23 | Jim Smith Invitational | 2019 |
| 11 | 7:40.80 | Jimmy MintelCenter Moriches | Center Moriches '22 | Bob Pratt Cross Country Invitational | 2018 |
| 12 | 7:43.80 | Christopher WeiderSmithtown West | Smithtown West '15 | Suffolk Coaches XC Invitational | 2011 |
| 13 | 7:44.01 | Gavin EhlersWesthampton Beach | Westhampton Beach '22 | Jim Smith Results - Boys | |
| 14 | 7:44.86 | Cooper SchochPort Jefferson | Port Jefferson '21 | Bob Pratt Cross Country Invitational | 2017 |
| 15 | 7:45.14 | Thomas LouroSt. Anthony's | St. Anthony's '14 | NSCHSAA League Championships | 2010 |
| 16 | 7:45.17 | Gregory DiemSt. Anthony's | St. Anthony's '15 | NSCHSAA League Championships | 2011 |
| 17 | 7:45.87 | Zac MobiusSouthampton | Southampton '21 | Bob Pratt Cross Country Invitational | 2017 |
| 18 | 7:46.10 | Timothy MonahanConnetquot | Connetquot '16 | Jim Smith Invitational | 2012 |
| 19 | 7:46.93 | Ryan DearieSt. Anthony's | St. Anthony's '16 | Saint Anthony's Cross Country Invitational | 2012 |
| 20 | 7:47.09 | Grant SamaraPort Jefferson | Port Jefferson '21 | Bob Pratt Cross Country Invitational | 2017 |
| 21 | 7:47.10 | Patrick GintySmithtown East | Smithtown East '13 | Jim Smith Invitational | 2009 |
| 22 | 7:47.42 | Patrick FiorilloSt. John the Baptist | St. John the Baptist '20 | NSCHSAA League Championships | 2016 |
| 23 | 7:47.43 | Michael DoneganCenter Moriches | Center Moriches '19 | Suffolk Officials XC Invitational | 2015 |
| 24 | 7:47.69 | Patrick KainSt. John the Baptist | St. John the Baptist '18 | NSCHSAA League Championships | 2014 |
| 25 | 7:48.02 | Chris RotanzWard Melville | Ward Melville '20 | Suffolk Officials XC Invitational | 2016 |
| 26 | 7:48.23 | Jason GuintaBayport-Blue Point | Bayport-Blue Point '16 | Suffolk Coaches Invitational | 2012 |
| 27 | 7:48.38 | Aidan HealySt. John the Baptist | St. John the Baptist '18 | NSCHSAA League Championships | 2014 |
| 28 | 7:48.78 | John McMullinSt. Anthony's | St. Anthony's '14 | NSCHSAA League Championships | 2010 |
| 29 | 7:48.79 | William MaloneSouthampton | Southampton '22 | Jim Smith Results - Boys | |
| 30 | 7:49.95 | Owen McCarthySt. Anthony's | St. Anthony's '20 | Saint Anthony's Cross Country Invitational | 2016 |
| 31 | 7:50.07 | Thomas FodorNorthport | Northport '20 | Jim Smith Invitational | 2016 |
| 32 | 7:50.09 | Frederick BuckholtzSt. Anthony's | St. Anthony's '16 | Saint Anthony's Cross Country Invitational | 2012 |
| 33 | 7:50.13 | Joshua HadityCommack | Commack '15 | Jim Smith Invitational | 2011 |
| 34 | 7:50.43 | Michael Barbaro-BarSt. Anthony's | St. Anthony's '19 | NSCHSAA League Championships | 2015 |
| 35 | 7:50.86 | John LeeShoreham-Wading River | Shoreham-Wading River '12 | Bob Pratt Cross Country Invitational | 2008 |
| 36 | 7:51.16 | James RicciHarborfields | Harborfields '23 | Jim Smith Invitational | 2019 |
| 37 | 7:51.31 | Ryan CannonSt. Anthony's | St. Anthony's '14 | NSCHSAA League Championships | 2010 |
| 38 | 7:51.44 | Brian WindischWalt Whitman | Walt Whitman '13 | Jim Smith Invitational | 2009 |
| 39 | 7:51.81 | Zachary CammerWalt Whitman | Walt Whitman '13 | Jim Smith Invitational | 2009 |
| 40 | 7:52.27 | Andrew FreedmanHalf Hollow Hills East | Half Hollow Hills East '14 | Suffolk Coaches XC Invitational | 2010 |
| 41 | 7:52.76 | Nick ScheinerBellport | Bellport '21 | Suffolk Officials XC Invitational | 2017 |
| 42 | 7:53.80 | Fernando SanchezSt. John the Baptist | St. John the Baptist '21 | NSCHSAA League Championships | 2017 |
| 43 | 7:54.19 | Patrick TeeseSmithtown East | Smithtown East '15 | Suffolk Coaches XC Invitational | 2011 |
| 44 | 7:54.31 | Emilo EspinozaEast Hampton | East Hampton '18 | Jim Smith Invitational | 2014 |
| 45 | 7:54.45 | Robert DohertySt. Anthony's | St. Anthony's '21 | NSCHSAA League Championships | 2017 |
| 46 | 7:54.54 | Matthew GladyszShoreham-Wading River | Shoreham-Wading River '15 | Suffolk Coaches XC Invitational | 2011 |
| 47 | 7:54.68 | Trevor HayesWesthampton Beach | Westhampton Beach '24 | Jim Smith Invitational | 2019 |
| 48 | 7:54.84 | Ryan ColabellaHauppauge | Hauppauge '12 | Bob Pratt Cross Country Invitational | 2008 |
| 49 | 7:54.94 | Matthew ClarkeSt. Anthony's | St. Anthony's '15 | Saint Anthony's Cross Country Invitational | 2011 |
| 50 | 7:55.01 | Joseph KeaneSt. Anthony's | St. Anthony's '15 | NSCHSAA League Championships | 2011 |
| 51 | 7:55.85 | Engstrom ErikEast Hampton | East Hampton '16 | Saint Anthony's Cross Country Invitational | 2012 |
| 52 | 7:56.04 | Andrew NicholsonWard Melville | Ward Melville '22 | Saint Anthony's Cross Country Invitational | 2018 |
| 53 | 7:56.09 | Philip PoloSt. Anthony's | St. Anthony's '19 | NSCHSAA League Championships | 2015 |
| 54 | 7:56.69 | Evan PurdyShoreham-Wading River | Shoreham-Wading River '13 | Jim Smith Invitational | 2009 |
| 55 | 7:56.82 | Matthew GenoveseSt. Anthony's | St. Anthony's '16 | Saint Anthony's Cross Country Invitational | 2012 |
| 56 | 7:56.97 | Fletcher HozvenWard Melville | Ward Melville '21 | Saint Anthony's Cross Country Invitational | 2017 |
| 57 | 7:57.04 | Kyle AntonucciWard Melville | Ward Melville '15 | Suffolk Officials XC Invitational | 2011 |
| 58 | 7:57.24 | JyShawn WilkinsEast Islip | East Islip '21 | Bob Pratt Cross Country Invitational | 2017 |
| 59 | 7:57.65 | Derek SmithHarborfields | Harborfields '15 | Suffolk Officials XC Invitational | 2011 |
| 60 | 7:57.95 | George MaidhofSmithtown West | Smithtown West '21 | Bob Pratt Cross Country Invitational | 2017 |
| 61 | 7:58.25 | Victor GarifoBayport-Blue Point | Bayport-Blue Point '16 | Suffolk Coaches Invitational | 2012 |
| 62 | 7:58.31 | Andrew AraneoWard Melville | Ward Melville '21 | Suffolk Officials XC Invitational | 2016 |
| 63 | 7:58.37 | Robert KellyConnetquot | Connetquot '13 | Jim Smith Invitational | 2009 |
| 64 | 7:58.60 | Charles HetterichWest Islip | West Islip '16 | Jim Smith Invitational | 2012 |
| 65 | 7:58.87 | Sebastian Hunter CuyjetSouthampton | Southampton '16 | Bob Pratt Cross Country Invitational | 2012 |
| 66 | 7:58.88 | Artemi GavalasSouthampton | Southampton '20 | Bob Pratt Boys Results | |
| 67 | 7:59.21 | Cole ManeyHarborfields | Harborfields '22 | Saint Anthony's Cross Country Invitational | 2018 |
| 68 | 7:59.38 | Chris TintiSt. John the Baptist | St. John the Baptist '16 | NSCHSAA League Championships | 2012 |
| 69 | 7:59.86 | Richard PleasantsHalf Hollow Hills East | Half Hollow Hills East '19 | Jim Smith Invitational | 2015 |
| 70 | 8:00.03 | Aiden HellerHuntington | Huntington '21 | Suffolk Officials XC Invitational | 2017 |
| 71 | 8:00.20 | Dan InfrancoRocky Point | Rocky Point '16 | Jim Smith Invitational | 2012 |
| 72 | 8:00.87 | Julian CorbeauxNorthport | Northport '19 | Jim Smith Invitational | 2015 |
| 73 | 8:00.88 | Kyle O'BrienHuntington | Huntington '16 | Suffolk Officials XC Invitational | 2012 |
| 74 | 8:00.90 | Nick CaruanaSachem East | Sachem East '16 | Suffolk Coaches Invitational | 2012 |
| 75 | 8:01.10 | Gareth SchaeferNorthport | Northport '14 | Suffolk Coaches XC Invitational | 2010 |
| 76 | 8:01.16 | Justin MarroSouthampton | Southampton '22 | Bob Pratt Cross Country Invitational | 2018 |
| 77 | 8:01.44 | Ramin HerathHalf Hollow Hills East | Half Hollow Hills East '20 | Jim Smith Invitational | 2016 |
| 78 | 8:01.45 | Ryan FanWard Melville | Ward Melville '15 | Suffolk Officials XC Invitational | 2011 |
| 79 | 8:01.51 | Wyeth SemoNorthport | Northport '22 | Bob Pratt Cross Country Invitational | 2018 |
| 80 | 8:01.72 | Thomas MeehanEastport-South Manor | Eastport-South Manor '14 | Suffolk Coaches XC Invitational | 2010 |
| 81 | 8:01.82 | Jake RussoConnetquot | Connetquot '16 | Suffolk Coaches Invitational | 2012 |
| 82 | 8:01.96 | Brian VeitPort Jefferson | Port Jefferson '21 | Bob Pratt Cross Country Invitational | 2017 |
| 83 | 8:02.04 | Stephen EgerSt. Anthony's | St. Anthony's '20 | NSCHSAA League Championships | 2016 |
| 84 | 8:02.10 | Joe WetzelNorthport | Northport '15 | Suffolk Coaches XC Invitational | 2011 |
| 85 | 8:02.49 | Joseph ZimblerSmithtown East | Smithtown East '21 | Bob Pratt Cross Country Invitational | 2017 |
| 86 | 8:02.57 | Tim McGowanNorthport | Northport '14 | Suffolk Coaches XC Invitational | 2010 |
| 87 | 8:02.64 | Ryan CarrickRiverhead | Riverhead '19 | Jim Smith Invitational | 2015 |
| 88 | 8:02.97 | Ryan KerwickSt. Anthony's | St. Anthony's '14 | NSCHSAA League Championships | 2010 |
| 89 | 8:03.00 | Charles FriedelWest Babylon | West Babylon '22 | Bob Pratt Cross Country Invitational | 2018 |
| 90 | 8:03.10 | Andrew AzzaraHarborfields | Harborfields '18 | Bob Pratt Cross Country Invitational | 2014 |
| 91 | 8:03.22 | Danny RyanWard Melville | Ward Melville '18 | Suffolk Officials XC Invitational | 2014 |
| 92 | 8:03.39 | Kevin CawleySmithtown East | Smithtown East '19 | Bob Pratt Cross Country Invitational | 2015 |
| 93 | 8:03.41 | Liam MacciHarborfields | Harborfields '14 | Suffolk Officials XC Invitational | 2010 |
| 94 | 8:03.52 | Michael CatalanoSmithtown West | Smithtown West '12 | Bob Pratt Cross Country Invitational | 2008 |
| 95 | 8:03.59 | Brendan DearieSt. Anthony's | St. Anthony's '19 | NSCHSAA League Championships | 2015 |
| 96 | 8:03.62 | Andrew ShaefferDeer Park | Deer Park '14 | Suffolk Officials XC Invitational | 2010 |
| 97 | 8:04.15 | Louis SantelliSt. Anthony's | St. Anthony's '14 | NSCHSAA League Championships | 2010 |
| 98 | 8:04.16 | Brian KreiderSt. Anthony's | St. Anthony's '14 | NSCHSAA League Championships | 2010 |
| 99 | 8:04.17 | Brendan AndersonSt. John the Baptist | St. John the Baptist '18 | NSCHSAA League Championships | 2014 |
| 100 | 8:04.38 | Marcos PerivolarisMattituck | Mattituck '15 | Jim Smith Invitational | 2011 |
