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| 2022 |
| Class: 1A | | Round 1 | | Millry (30-1, 12-2) Woodland. Woodland loses series (0-2) |
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| 2021 |
| Class: 1A | | Round 1 | | Woodland (16-1, 13-1) Central Hayneville. Woodland wins series (2-0) | | Round 2 | | Sweet Water (13-3, 8-2) Woodland. Woodland loses series (0-2) |
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| 2012 |
| Class: 2A | | Round 1 | | Woodland (7-1, 5-0) Vincent. Woodland wins series (2-0) | | Round 2 | | Woodland (5-0, 5-1) Ranburne. Woodland wins series (2-0) | | Round 3 | | American Christian (6-1, 5-0) Woodland. Woodland loses series (0-2) |
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| 2011 |
| Class: 2A | | Round 1 | | Woodland (16-4, 8-6) Victory Christian. Woodland wins series (2-0) | | Round 2 | | Lineville (4-1, 8-1) Woodland. Woodland loses series (0-2) |
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| 2010 |
| Class: 2A | | Round 1 | | Thorsby (10-0, 22-5) Woodland. Woodland loses series (0-2) |
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| 2009 |
| Class: 2A | | Round 1 | | Shades Mountain Christian (10-5, 10-6) Woodland. Woodland loses series (0-2) |
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| 2004 |
| Class: 2A | | Round 1 | | Geneva County (2-1) Woodland. |
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| 2003 |
| Class: 2A | | Round 1 | | Woodland (11-0) Luverne. | | Round 2 | | Excel (6-3) Woodland. |
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| 2002 |
| Class: 1A | | Round 1 | | Woodland (4-3) Warrior. | | Round 2 | | Woodland (7-3) Berry Fayette. | | Round 3 | | Athens Bible (3-0, 10-1) Woodland. Woodland loses series (0-2) |
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| 2001 |
| Class: 1A | | Round 1 | | Woodland (10-9) Cedar Bluff. | | Round 2 | | Collinsville (3-1) Woodland. |
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| 1996 |
| Class: 2A | | Round 1 | | Straughn (11-3) Woodland. |
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| 1984 |
| Class: 1A | | Round 1 | | Woodland (13-1) Pleasant Valley. | | Round 2 | | Collinsville (9-8) Woodland. |
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| 1983 |
| Class: 1A | | Round 1 | | Talladega County Central (5-4) Woodland. |
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