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Winchester Red & Black
Varsity Football
Winchester, MA
243Followers
25-26

Overall

0-0

League

0-0 (1st)

MA Rank

79
2025-26 V. Football
Fall 25-26Fall 25-26Fall 25-26Fall 24-25Fall 24-25Fall 24-25Fall 23-24Fall 23-24Fall 23-24Fall 22-23Fall 22-23Fall 21-22Fall 21-22Fall 21-22Fall 20-21Fall 20-21Fall 20-21Fall 19-20Fall 19-20Fall 19-20Fall 18-19Fall 18-19Fall 18-19Fall 17-18Fall 17-18Fall 17-18Fall 16-17Fall 16-17Fall 16-17Fall 15-16Fall 15-16Fall 15-16Fall 14-15Fall 14-15Fall 14-15Fall 13-14Fall 13-14Fall 13-14Fall 12-13Fall 12-13Fall 12-13Fall 11-12Fall 11-12Fall 11-12Fall 10-11Fall 10-11Fall 10-11Fall 09-10Fall 08-09Fall 07-08Fall 06-07Fall 05-06Fall 04-05

Winchester Football History

Previous SeasonsAll-Time Roster

  • 2025-26

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 2
    • Overall Record: 0-0
    • League Record: 0-0
    • DMA Rank: 84
    • State Rank: 79
    • State Division Rank: 11

  • 2024-25

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 2
    • Overall Record: 8-3
    • League Record: 4-1
    • DMA Rank: 61
    • State Rank: 54
    • State Division Rank: 8

  • 2023-24

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 2
    • Overall Record: 8-3
    • League Record: 3-2
    • DMA Rank: 65
    • State Rank: 57
    • State Division Rank: 8

  • 2022-23

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 2
    • Overall Record: 3-8
    • League Record: 1-4
    • DMA Rank: 202
    • State Rank: 170
    • State Division Rank: 28

  • 2021-22

    Head Coach: Walter Dembowski
    • League: Middlesex - Liberty
    • Division: Division 2
    • Overall Record: 1-9
    • League Record: 1-4
    • DMA Rank: 265
    • State Rank: 233
    • State Division Rank: 32

  • 2020-21

    Head Coach: John Dunleavy
    • League: Middlesex - Liberty
    • Division: Division North 3
    • Overall Record: 2-4
    • League Record: 2-3
    • DMA Rank: 146
    • State Rank: 139
    • State Division Rank: 8

  • 2019-20

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division North 3
    • Overall Record: 9-2
    • League Record: 4-1
    • DMA Rank: 43
    • National Rank: 2981
    • State Rank: 38
    • State Division Rank: 4

  • 2018-19

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 3
    • Overall Record: 6-5
    • League Record: 2-3
    • DMA Rank: 112
    • National Rank: 5306
    • State Rank: 109
    • State Division Rank: 26

  • 2017-18

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 3
    • Overall Record: 3-8
    • League Record: 2-3
    • DMA Rank: 161
    • National Rank: 8458
    • State Rank: 150
    • State Division Rank: 27

  • 2016-17

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 2
    • Overall Record: 5-7
    • League Record: 1-4
    • DMA Rank: 132
    • National Rank: 6577
    • State Rank: 123
    • State Division Rank: 25

  • 2015-16

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 3
    • Overall Record: 5-7
    • League Record: 1-4
    • DMA Rank: 147
    • National Rank: 7058
    • State Rank: 139
    • State Division Rank: 33

  • 2014-15

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 3
    • Overall Record: 3-8
    • League Record: 1-4
    • DMA Rank: 119
    • National Rank: 6096
    • State Rank: 109
    • State Division Rank: 23

  • 2013-14

    Head Coach: -
    • League: Middlesex - Liberty
    • Division: Division 3
    • Overall Record: 3-8
    • League Record: 1-3
    • DMA Rank: 161
    • National Rank: 8218
    • State Rank: 155
    • State Division Rank: 31

  • 2012-13

    Head Coach: -
    • League: Middlesex - Large
    • Division: Division E-2
    • Overall Record: 3-8
    • League Record: 0-5
    • DMA Rank: 214
    • National Rank: 10492
    • State Rank: 213
    • State Division Rank: 22

  • 2011-12

    Head Coach: Wally Dembowski
    • League: Middlesex - Large
    • Division: Division E-2
    • Overall Record: 1-9
    • League Record: 0-5
    • DMA Rank: 244
    • National Rank: 11793
    • State Rank: 245
    • State Division Rank: 21

  • 2010-11

    Head Coach: -
    • League: Middlesex - Large
    • Division: Division E-2
    • Overall Record: 5-6
    • League Record: 1-3
    • DMA Rank: 126
    • National Rank: 7126
    • State Rank: 121
    • State Division Rank: 19

  • 2009-10

    Head Coach: Paul Sobolewski
    • League: Middlesex
    • Division: Division E-2
    • Overall Record: 9-2
    • League Record: 7-1
    • DMA Rank: 34
    • National Rank: 3129
    • State Rank: 28
    • State Division Rank: 8

  • 2008-09

    Head Coach: Paul Sobolewski
    • League: Middlesex
    • Division: Division E-2
    • Overall Record: 5-6
    • League Record: 2-6
    • DMA Rank: 130
    • National Rank: 8157
    • State Rank: 119
    • State Division Rank: 14

  • 2007-08

    Head Coach: Paul Sobolewski
    • League: Middlesex
    • Division: -
    • Overall Record: 6-5
    • League Record: 4-4
    • DMA Rank: 71
    • National Rank: 3610
    • State Rank: 74

  • 2006-07

    Head Coach: Paul Sobolewski
    • League: Middlesex
    • Division: -
    • Overall Record: 5-6
    • League Record: 4-5
    • DMA Rank: 85
    • National Rank: 3747
    • State Rank: 87

  • 2005-06

    Head Coach: John Donohue
    • League: Middlesex
    • Division: -
    • Overall Record: 3-8
    • League Record: 3-6
    • DMA Rank: 160
    • National Rank: 6742
    • State Rank: 158

  • 2004-05

    Head Coach: Paul Sobolewski
    • League: Middlesex
    • Division: -
    • Overall Record: 3-7
    • League Record: 3-6
    • DMA Rank: 208
    • National Rank: 9778
    • State Rank: 200
W
Winchester High School
80 Skillings Rd
Winchester, MA 01890
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