Winchester Red & Black
Varsity Football
Winchester, MA
243Followers
Apps
MaxPrepsFollow your favorite high school teams and players
MP Stats for iPadStat keeping for basketball teams
Pro Photography
Watch
Content Contributors
W
25-26
Overall
0-0
League
0-0 (1st)
NAT Rank
4377
MA Rank
78
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
2025-26
Head Coach: -- League: Middlesex - Liberty
- Division: Division 2
- Overall Record: 0-0
- League Record: 0-0
- DMA Rank: 85
- National Rank: 4377
- State Rank: 78
- State Division Rank: 12
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
© 2025 MaxPreps, Inc.
MaxPreps is a registered trademark of MaxPreps, Inc.