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| 2008 |
| Class: 5A | | Round 1 | | Pleasant Grove (5-2, 5-0) Woodlawn. Woodlawn loses series (0-2) |
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| 2007 |
| Class: 5A | | Round 1 | | Mortimer Jordan (10-0) Woodlawn. |
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| 1991 |
| Class: 6A | | Round 1 | | West End (10-1) Woodlawn. |
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| 1987 |
| Class: 5A | | Round 1 | | Midfield (16-7) Woodlawn. |
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| 1959 |
| Class: A | | Round 1 | | Woodlawn (4-3) Tuscaloosa. | | Round 2 | | Woodlawn (6-1) Sheffield. | | Round 3 | | Woodlawn (4-1) Anniston. | | 4 | | Woodlawn (6-0, 1-4, 12-0) Jackson. Woodlawn wins series (2-1) |
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| 1956 |
| Class: A | | Round 1 | | Woodlawn (9-2) Montevallo. | | Round 2 | | Woodlawn (6-4) Coffee. | | Round 3 | | Woodlawn (6-0) Childersburg. | | 4 | | Woodlawn (6-7, 6-5, 3-1) Demopolis. Woodlawn wins series (2-1) |
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| 1955 |
| Class: A | | Round 1 | | Woodlawn (6-4) Montevallo. | | Round 2 | | Cullman (4-2) Woodlawn. |
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| 1949 |
| Class: A | | Round 1 | | Woodlawn () Tuscaloosa. | | Round 2 | | Woodlawn (2-1) Sidney Lanier. | | Round 3 | | Woodlawn (5-3) Rison. | | 4 | | Woodlawn (6-1) Coffee. |
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