Winchester Basketball History

  • 2025-26

    Head Coach: -
    • League: Middlesex
    • Division: Division 1
    • Overall Record: 0-0
    • League Record: 0-0
  • 2024-25

    Head Coach: -
    • League: Middlesex
    • Division: Division 1
    • Overall Record: 16-5
    • League Record: 13-2
    • State Division Rank: 20
    • DMA Rank: 43
    • State Rank: 48
  • 2023-24

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 1
    • Overall Record: 13-9
    • League Record: 10-7
    • DMA Rank: 111
    • State Rank: 102
    • State Division Rank: 41
  • 2022-23

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 1
    • Overall Record: 15-9
    • League Record: 9-6
    • DMA Rank: 76
    • State Rank: 80
    • State Division Rank: 33
  • 2021-22

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 1
    • Overall Record: 18-6
    • League Record: 10-5
    • DMA Rank: 25
    • State Rank: 24
    • State Division Rank: 15
  • 2020-21

    Head Coach: John Dunleavy
    • League: Middlesex
    • Division: Division North 2
    • Overall Record: 11-3
    • League Record: 6-1
    • State Rank: 27
    • State Division Rank: 2
  • 2019-20

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division North 2
    • Overall Record: 16-9
    • League Record: 11-6
    • DMA Rank: 94
    • National Rank: 6179
    • State Rank: 96
    • State Division Rank: 7
  • 2018-19

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division North 2
    • Overall Record: 10-11
    • League Record: 6-10
    • DMA Rank: 128
    • National Rank: 7283
    • State Rank: 123
    • State Division Rank: 12
  • 2017-18

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 15-9
    • League Record: 10-6
    • DMA Rank: 91
    • National Rank: 5524
    • State Rank: 78
    • State Division Rank: 21
  • 2016-17

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 13-11
    • League Record: 9-7
    • DMA Rank: 93
    • National Rank: 5624
    • State Rank: 93
    • State Division Rank: 20
  • 2015-16

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 9-13
    • League Record: 6-10
    • DMA Rank: 178
    • National Rank: 8815
    • State Rank: 170
    • State Division Rank: 51
  • 2014-15

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 14-8
    • League Record: 9-7
    • DMA Rank: 91
    • National Rank: 4797
    • State Rank: 91
    • State Division Rank: 26
  • 2013-14

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 4-8
    • League Record: 3-7
    • DMA Rank: 135
    • National Rank: 6205
    • State Rank: 138
    • State Division Rank: 37
  • 2012-13

    Head Coach: John Fleming
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 11-9
    • League Record: 8-7
    • DMA Rank: 116
    • National Rank: 5891
    • State Rank: 128
    • State Division Rank: 28
  • 2011-12

    Head Coach: Quiton Dale
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 3-17
    • League Record: 3-13
    • DMA Rank: 200
    • National Rank: 8758
    • State Rank: 203
    • State Division Rank: 47
  • 2010-11

    Head Coach: Quiton Dale
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 11-10
    • League Record: 10-7
    • DMA Rank: 66
    • National Rank: 3327
    • State Rank: 67
    • State Division Rank: 12
  • 2009-10

    Head Coach: Quiton Dale
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 5-17
    • League Record: 4-14
    • DMA Rank: 195
    • National Rank: 8582
    • State Rank: 193
    • State Division Rank: 50
  • 2008-09

    Head Coach: -
    • League: Middlesex
    • Division: Division 2
    • Overall Record: 1-17
    • League Record: 1-17
    • DMA Rank: 189
    • National Rank: 8356
    • State Rank: 195
    • State Division Rank: 53
  • 2007-08

    Head Coach: Winchester Coach
    • League: Middlesex
    • Division: -
    • Overall Record: 10-12
    • League Record: 9-10
    • DMA Rank: 94
    • National Rank: 4108
    • State Rank: 94
  • 2006-07

    Head Coach: -
    • League: Middlesex
    • Division: -
    • Overall Record: 7-12
    • League Record: 7-10
    • DMA Rank: 125
    • National Rank: 4889
    • State Rank: 120
  • 2005-06

    Head Coach: -
    • League: Middlesex
    • Division: -
    • Overall Record: 12-8
    • League Record: 6-7
    • DMA Rank: 34
    • National Rank: 2120
    • State Rank: 34
W
Winchester High School
80 Skillings Rd
Winchester, MA 01890
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