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| 2023 |
| Class: 2A | | Round 1 | | Pike Liberal Arts (0-1, 15-5, 9-2) Cottonwood. Cottonwood loses series (1-2) |
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| 2022 |
| Class: 2A | | Round 1 | | Vincent (5-0, 2-1) Cottonwood. Cottonwood loses series (0-2) |
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| 2021 |
| Class: 2A | | Round 1 | | Cottonwood (10-0, 3-8, 11-10) Clarke County. Cottonwood wins series (2-1) | | Round 2 | | Cottonwood (3-16, 8-2, 12-2) Luverne. Cottonwood wins series (2-1) | | Round 3 | | Ariton (17-1, 13-3) Cottonwood. Cottonwood loses series (0-2) |
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| 2019 |
| Class: 2A | | Round 1 | | Ariton (1-3, 12-2, 17-2) Cottonwood. |
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| 2018 |
| Class: 2A | | Round 1 | | Cottonwood (0-4, 2-1, 12-11) Washington County. | | Round 2 | | St. Lukes (15-3, 6-10, 12-2) Cottonwood. |
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| 2017 |
| Class: 2A | | Round 1 | | Cottonwood (6-1, 1-0) Horseshoe Bend. Cottonwood wins series (2-0) | | Round 2 | | St. Lukes (0-2, 3-1, 19-3) Cottonwood. Cottonwood loses series (1-2) |
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| 2009 |
| Class: 2A | | Round 1 | | Flomaton (10-11, 14-2, 11-5) Cottonwood. Cottonwood loses series (1-2) |
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| 2008 |
| Class: 2A | | Round 1 | | Wicksburg (13-1, 6-5) Cottonwood. Cottonwood loses series (0-2) |
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| 2003 |
| Class: 1A | | Round 1 | | Millry (9-0) Cottonwood. |
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| 1999 |
| Class: 2A | | Round 1 | | Maplesville (8-7) Cottonwood. |
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| 1989 |
| Class: 2A | | Round 1 | | Cottonwood (6-0) Straughn. | | Round 2 | | Cottonwood (2-1) Alabama Christian. | | Round 3 | | Flomaton (9-4) Cottonwood. |
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| 1988 |
| Class: 2A | | Round 1 | | Cottonwood (15-7) Samson. | | Round 2 | | Flomaton (2-1) Cottonwood. |
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| 1987 |
| Class: 2A | | Round 1 | | Cottonwood (13-3) Samson. | | Round 2 | | Cottonwood (12-4) Marengo. | | Semi-finals | | Cottonwood (7-6, 10-8) Holtville. Cottonwood wins series (2-0) | | Finals | | Cottonwood (4-1, 7-3) Red Bay. Cottonwood wins series (2-0) |
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| 1986 |
| Class: 2A | | Round 1 | | Cottonwood (29-1) Straughn. | | Round 2 | | Cottonwood (18-2) Marengo. | | Semi-finals | | Cottonwood (24-1, 12-0) Talladega County Central. Cottonwood wins series (2-0) | | Finals | | Cottonwood (2-1, 7-4) Northside. Cottonwood wins series (2-0) |
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| 1985 |
| Class: 2A | | Round 1 | | Cottonwood (7-2) Goshen. | | Round 2 | | Cottonwood (7-1) Flomaton. | | Semi-finals | | Cottonwood (5-0, 6-14, 11-3) Catholic Montgomery. Cottonwood wins series (2-1) | | Finals | | Cottonwood (4-3, 1-0) Northside. Cottonwood wins series (2-0) |
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| 1982 |
| Class: 2A | | Round 1 | | Cottonwood (9-3) Goshen. | | Round 2 | | J.F. Shields (4-1) Cottonwood. |
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| 1981 |
| Class: 2A | | Round 1 | | Cottonwood (8-1) Luverne. | | Round 2 | | Cottonwood (8-4) McIntosh. | | Semi-finals | | Cottonwood (12-4, 8-6) Dadeville. Cottonwood wins series (2-0) | | Finals | | Cottonwood (7-8, 5-7, 12-6) Stevenson. Cottonwood wins series (2-1) |
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| 1978 |
| Class: 2A | | Round 1 | | Cottonwood () . | | Round 2 | | St. Pauls (2-1) Cottonwood. |
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| 1974 |
| Class: 1A/2A | | Round 2 | | Cottonwood () . | | Semi-finals | | Baker (5-0, 6-5) Cottonwood. Cottonwood loses series (0-2) |
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| 1971 |
| Class: 1A/2A | | Round 1 | | Cottonwood () . | | Round 2 | | Autaugaville (7-0) Cottonwood. |
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| 1970 |
| Class: 1A/2A | | Round 1 | | Cottonwood () . | | Round 2 | | Bullock County (9-3) Cottonwood. |
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