| 1 | 2:27.70 | Mike BranniganNorthport | Northport '15 | Indoor Track & Field Championships | 2014 |
| 2 | 2:29.00 | Isaiah ClaiborneNorthport | Northport '18 | Long Island Elite Track Invitational | 2018 |
| 3 | 2:29.61 | Matthew PayampsSt. Anthony's | St. Anthony's '19 | Long Island Elite Track Invitational | 2018 |
| 4 | 2:30.35 | Charlie TheissWard Melville | Ward Melville '15 | Long Island Elite Track Invitational | 2015 |
| 5 | 2:30.45 | Christopher TibbettsSachem North | Sachem North '17 | Section XI Indoor State Qualifier Meet | 2017 |
| 6 | 2:30.63 | Shamar PowellWalt Whitman | Walt Whitman '15 | Section XI Indoor State Qualifier Meet | 2015 |
| 7 | 2:31.18 | Luciano FioreBay Shore | Bay Shore '15 | Section XI Boys Indoor League Championships | 2015 |
| 8 | 2:31.72 | Aiden SmythWalt Whitman | Walt Whitman '18 | Long Island Elite Track Invitational | 2018 |
| 9 | 2:32.58 | Juan LassoWesthampton Beach | Westhampton Beach '19 | Long Island Elite Track Invitational | 2018 |
| 10 | 2:32.60 | Anthony CocciaSachem North | Sachem North '14 | Long Island Elite Track Invitational | 2014 |
| 11 | 2:32.94 | Kal LewisShelter Island | Shelter Island '20 | Section XI Boys Crossover E | 2019 |
| 12 | 2:33.13 | Eric CunhaRiverhead | Riverhead '17 | Section XI Indoor State Qualifier Meet | 2017 |
| 13 | 2:33.20 | Frank FezzaSachem North | Sachem North '09 | Boys Crossover Meet B | 2008 |
| 14 | 2:33.20 | Andrew SenfWard Melville | Ward Melville '27 | Section XI BOYS League 2 Championship | 2026 |
| 15 | 2:33.28 | Danny RyanWard Melville | Ward Melville '18 | Section XI Indoor State Qualifier Meet | 2017 |
| 16 | 2:33.52 | Cullen ArmstrongHauppauge | Hauppauge '17 | Section XI Indoor State Qualifier Meet | 2017 |
| 17 | 2:33.84 | Christopher TibbetSachem North | Sachem North '17 | Long Island Elite Track Invitational | 2016 |
| 18 | 2:34.01 | Matthew WhalenSmithtown East | Smithtown East '15 | Section XI Indoor State Qualifier Meet | 2015 |
| 19 | 2:34.02 | Ryan DonohueIslip | Islip '26 | Section XI State Qualifer Meet Day 2 | 2026 |
| 20 | 2:34.11 | Nick BeglaneHauppauge | Hauppauge '16 | Section XI Boys Small School Championships | 2016 |
| 21 | 2:34.18 | Jon SeyfertWard Melville | Ward Melville '25 | Section XI BOYS Crossover C Meet 3 | 2024 |
| 22 | 2:34.43 | Nicholas DiCaprioMiller Place | Miller Place '27 | Section XI BOYS Small School County Championships | 2026 |
| 23 | 2:34.47 | Jake AlbertLindenhurst | Lindenhurst '25 | BOYS League Championships 2 | 2025 |
| 24 | 2:34.64 | Alex ToranNorthport | Northport '26 | BOYS League Championships 2 | 2025 |
| 25 | 2:34.66 | Joseph LicataNorth Babylon | North Babylon '25 | BOYS League Championships 2 | 2025 |
| 26 | 2:34.75 | Ryan FowkesEast Hampton | East Hampton '19 | Section XI Boys Small School Championships | 2019 |
| 27 | 2:34.84 | Kevin KreiderSt. Anthony's | St. Anthony's '12 | NSCHSAA Indoor League Championships | 2012 |
| 28 | 2:34.86 | Justin AlbaneseEastport-South Manor | Eastport-South Manor '25 | BOYS Small Schools County Championships | 2025 |
| 29 | 2:34.88 | Rory HanniganSt. John the Baptist | St. John the Baptist '15 | NSCHSAA Indoor League Championships | 2015 |
| 30 | 2:35.01 | Nick FentonDeer Park | Deer Park '17 | Section XI Indoor State Qualifier Meet | 2017 |
| 31 | 2:35.14 | Jake BurchamHalf Hollow Hills East | Half Hollow Hills East '14 | Section XI Boys Indoor League Championships | 2014 |
| 32 | 2:35.22 | Utsav DeshpandeSachem East | Sachem East '15 | Section XI Indoor State Qualifier Meet | 2015 |
| 33 | 2:35.37 | Chris OdinNorthport | Northport '13 | Section XI Large School Championships | 2013 |
| 34 | 2:35.48 | Michael HuebnerShoreham-Wading River | Shoreham-Wading River | BOYS Small Schools County Championships | 2025 |
| 35 | 2:35.49 | Ryan DearieSt. Anthony's | St. Anthony's '16 | NSCHSAA Christmas Classic | 2015 |
| 36 | 2:35.56 | Patrick TuckerSt. Anthony's | St. Anthony's '15 | Saint Anthony's Boys - Girls Developmental | 2015 |
| 37 | 2:35.58 | RJ PleasantsHalf Hollow Hills East | Half Hollow Hills East '19 | Section XI Boys Large School Championships | 2019 |
| 38 | 2:35.65 | Greg PerrierHalf Hollow Hills East | Half Hollow Hills East '11 | Section XI Indoor Track State Qualifier | 2011 |
| 39 | 2:35.70 | Micheal DanziSmithtown West | Smithtown West '20 | Long Island Elite Track Invitational | 2019 |
| 40 | 2:35.72 | Elijah ClaiborneNorthport | Northport '18 | Long Island Elite Track Invitational | 2018 |
| 41 | 2:35.73 | Brendan DearieSt. Anthony's | St. Anthony's '19 | Long Island Elite Track Invitational | 2019 |
| 42 | 2:35.80 | Andrew KeresztesPort Jefferson | Port Jefferson '12 | Section XI Small School Championships | 2012 |
| 43 | 2:35.80 | Charles HetterichWest Islip | West Islip '16 | Section XI Boys Large School Championships | 2015 |
| 44 | 2:35.94 | Andrew LunarolaComsewogue | Comsewogue '26 | Section XI State Qualifer Meet Day 2 | 2026 |
| 45 | 2:35.98 | Patrick AmbergerConnetquot | Connetquot '25 | BOYS League Championships 2 | 2025 |
| 46 | 2:35.99 | Alex LazarichSachem North | Sachem North '13 | Section XI Large School Championships | 2013 |
| 47 | 2:36.02 | Daniel SabiaSmithtown West | Smithtown West '20 | Section XI Boys Crossover E | 2020 |
| 48 | 2:36.09 | Carson CareySmithtown West | Smithtown West '25 | BOYS League 3 Championshp Meet | 2025 |
| 49 | 2:36.22 | Spencer LeeShoreham-Wading River | Shoreham-Wading River '27 | Section XI BOYS Crossover C (S3, S4) | 2025 |
| 50 | 2:36.31 | Nick CrociataHauppauge | Hauppauge '18 | Boys Crossover Meet E | 2017 |
| 51 | 2:36.36 | Dan O'ConnorNorthport | Northport '18 | Section XI Boys Large School Championships | 2018 |
| 52 | 2:36.44 | Luke CoulterRiverhead | Riverhead '16 | Boys Crossover Meet E | 2016 |
| 53 | 2:36.53 | Jeff ReyesBay Shore | Bay Shore '16 | Section XI Boys Large School Championships | 2016 |
| 54 | 2:36.54 | Aidan PiracciCommack | Commack '26 | Section XI BOYS Large School County Championships | 2026 |
| 55 | 2:36.63 | Tim McGowanNorthport | Northport '14 | Long Island Elite Track Invitational | 2014 |
| 56 | 2:36.68 | Nicholas ScheinerLongwood | Longwood '21 | Section XI Indoor State Qualifier Meet | 2019 |
| 57 | 2:36.75 | James BurkePort Jefferson | Port Jefferson '15 | Section XI Small School Championships | 2012 |
| 58 | 2:36.76 | Gavin DeVitoWest Islip | West Islip '25 | Section XI State Qualifier Meet (Day 1) | 2025 |
| 59 | 2:36.77 | Andrew FreedmanHalf Hollow Hills East | Half Hollow Hills East '14 | Section XI Indoor State Qualifier Meet | 2014 |
| 60 | 2:36.79 | Thomas FodorNorthport | Northport '20 | Long Island Elite Track Invitational | 2019 |
| 61 | 2:36.81 | Nicholas MuellersSmithtown West | Smithtown West '19 | Long Island Elite Track Invitational | 2018 |
| 62 | 2:36.94 | Gabriel KoNorthport | Northport '26 | Section XI State Qualifier Meet (Day 1) | 2025 |
| 63 | 2:36.95 | Jay SantanaWest Babylon | West Babylon '19 | Section XI Boys Indoor League Championships | 2019 |
| 64 | 2:37.15 | Charles BurchumHalf Hollow Hills East | Half Hollow Hills East '14 | Section XI Large School Championships | 2012 |
| 65 | 2:37.16 | Jonathan LauerSachem North | Sachem North '17 | Boys Crossover Meet D | 2017 |
| 66 | 2:37.42 | Timothy OdinNorthport | Northport '11 | Section XI Indoor Track State Qualifier | 2011 |
| 67 | 2:37.49 | Gavin EhlersWesthampton Beach | Westhampton Beach '22 | Section XI Boys Indoor League Championships | 2020 |
| 68 | 2:37.56 | Jack MorelliSt. Anthony's | St. Anthony's '24 | NSCHSAA Christmas Classic | 2023 |
| 69 | 2:37.57 | Thomas MeehanEastport-South Manor | Eastport-South Manor '14 | Section XI Small School Championships | 2012 |
| 70 | 2:37.58 | Dylan ManningCommack | Commack '25 | BOYS Coaches Classic | 2025 |
| 71 | 2:37.59 | Thomas LouroSt. Anthony's | St. Anthony's '14 | NSCHSAA Christmas Classic | 2012 |
| 72 | 2:37.74 | Kris MoranNorth Babylon | North Babylon '13 | Section XI Large School Championships | 2012 |
| 73 | 2:37.77 | Joshua GreenShelter Island | Shelter Island '18 | Section XI Indoor State Qualifier Meet | 2018 |
| 74 | 2:37.83 | Christian DuggalSouthampton | Southampton '25 | BOYS Small Schools County Championships | 2025 |
| 75 | 2:37.84 | David CabelloSmithtown West | Smithtown West '19 | Section XI Boys Indoor League Championships | 2018 |
| 76 | 2:37.85 | Eric HerrmannSmithtown East | Smithtown East '15 | Section XI Boys Crossover B | 2014 |
| 77 | 2:37.92 | Vincent Pitre JrBellport | Bellport | Section XI BOYS Crossover D Meet 1 | 2024 |
| 78 | 2:37.93 | Dylan HerathHalf Hollow Hills East (Hhh) | Half Hollow Hills East (Hhh) '27 | Section XI State Qualifer Meet Day 2 | 2026 |
| 79 | 2:37.94 | Thomas SchottMiller Place | Miller Place '17 | Boys Crossover Meet E | 2016 |
| 80 | 2:37.94 | William ReedEast Islip | East Islip '16 | Section XI Boys Last Chance Meet | 2015 |
| 81 | 2:38.02 | Ryan ScanlonHarborfields | Harborfields '16 | Boys Crossover Meet D | 2016 |
| 82 | 2:38.12 | Joseph TuckerSt. Anthony's | St. Anthony's '15 | NSCHSAA Indoor League Championships | 2015 |
| 83 | 2:38.14 | Ben MolinoCommack | Commack '25 | BOYS Large Schools County Championships | 2025 |
| 84 | 2:38.16 | Sean SmythWalt Whitman | Walt Whitman '18 | Section XI Boys Large School Championships | 2017 |
| 85 | 2:38.16 | Seamus TaylorNorthport | Northport '27 | BOYS League Championships 2 | 2025 |
| 86 | 2:38.20 | Angelo FelicianoBrentwood | Brentwood '25 | Section 11 State Quals | 2024 |
| 87 | 2:38.24 | Rob VietriBay Shore | Bay Shore '09 | Section XI Indoor Track & Field State Qualifi | 2009 |
| 88 | 2:38.29 | Christophe LangerSt. Anthony's | St. Anthony's | 2015 CHSAA Intersectional Freshmen & Sophomor | 2015 |
| 89 | 2:38.30 | Shawn WeigandNorthport | Northport '17 | Section XI Boys Large School Championships | 2016 |
| 90 | 2:38.38 | David HatchNorthport | Northport '13 | Section XI Boys Indoor League Championships | 2013 |
| 91 | 2:38.44 | Daniel CzopCommack | Commack '19 | Section XI Boys Last Chance Meet | 2019 |
| 92 | 2:38.44 | Brian HealySt. John the Baptist | St. John the Baptist '20 | Saint Anthony's Boys - Girls Developmental - Meet 3 | 2020 |
| 93 | 2:38.47 | Thomas AutinoComsewogue | Comsewogue '25 | BOYS League 3 Championshp Meet | 2025 |
| 94 | 2:38.48 | Sean RyanNorthport | Northport '19 | Section XI Boys Indoor League Championships | 2019 |
| 95 | 2:38.51 | Anthony LazaridisPatchogue-Medford | Patchogue-Medford '19 | Section XI Boys Indoor League Championships | 2019 |
| 96 | 2:38.52 | Shane McGuireHuntington | Huntington '17 | Section XI Indoor State Qualifier Meet | 2016 |
| 97 | 2:38.56 | Kyle MerberHalf Hollow Hills West | Half Hollow Hills West '08 | Boys Small School Championships | |
| 98 | 2:38.61 | Patrick MurphySt. Anthony's | St. Anthony's '10 | 2009 NSCHSAA Christmas Classic | 2009 |
| 99 | 2:38.62 | Kevin SullivanPort Jefferson | Port Jefferson '10 | Section XI Indoor Track & Field State Qualifi | 2009 |
| 100 | 2:38.62 | Christopher NamPort Jefferson | Port Jefferson '26 | Section XI State Qualifer Meet Day 2 | 2026 |
