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| 2024 |
| Class: 5A | | Round 1 | | Headland () Central Clay County. Headland wins series (2-0) | | Round 2 | | Holtville () Headland. Headland loses series (1-2) |
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| 2023 |
| Class: 5A | | Round 1 | | Headland (1-3, 14-3, 11-1) Greenville. Headland wins series (2-1) | | Round 2 | | Headland (18-4, 5-2) Sylacauga. Headland wins series (2-0) | | Round 3 | | Holtville (11-12, 4-2, 12-3) Headland. Headland loses series (1-2) |
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| 2022 |
| Class: 5A | | Round 1 | | Headland (14-3, 6-3) Marbury. Headland wins series (2-0) | | Round 2 | | Headland (7-1, 2-0) Elberta. Headland wins series (2-0) | | Round 3 | | Headland (3-2, 1-2, 10-3) Shelby County. Headland wins series (2-1) | | Semi-finals | | Holtville (4-2, 7-2) Headland. Headland loses series (0-2) |
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| 2021 |
| Class: 5A | | Round 1 | | Headland (2-1, 8-7) Elberta. Headland wins series (2-0) | | Round 2 | | Holtville (0-1, 5-2, 6-0) Headland. Headland loses series (1-2) |
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| 2019 |
| Class: 4A | | Round 1 | | Trinity (6-2, 3-0) Headland. |
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| 2018 |
| Class: 5A | | Round 1 | | Headland (3-1, 11-9) Jackson. | | Round 2 | | St. Pauls (2-3, 10-1, 8-4) Headland. |
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| 2017 |
| Class: 5A | | Round 1 | | Briarwood (13-1, 13-0) Headland. Headland loses series (0-2) |
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| 2016 |
| Class: 4A | | Round 1 | | UMS-Wright (14-0, 7-3) Headland. Headland loses series (0-2) |
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| 2015 |
| Class: 4A | | Round 1 | | Headland (9-1, 9-7) W.S. Neal. Headland wins series (2-0) | | Round 2 | | Headland (3-2, 3-2) UMS-Wright. Headland wins series (2-0) | | Round 3 | | Trinity (6-3, 4-2) Headland. Headland loses series (0-2) |
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| 2013 |
| Class: 4A | | Round 1 | | Alabama Christian (2-1, 7-2) Headland. Headland loses series (0-2) |
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| 2012 |
| Class: 4A | | Round 1 | | Alabama Christian (5-3, 8-0) Headland. Headland loses series (0-2) |
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| 2011 |
| Class: 4A | | Round 1 | | Headland (5-3, 3-13, 7-6) Alabama Christian. Headland wins series (2-0) | | Round 2 | | Straughn (10-2, 11-1) Headland. Headland loses series (0-2) |
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| 2010 |
| Class: 3A | | Round 1 | | Luverne (5-10, 1-9, 9-7) Headland. Headland loses series (0-2) |
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| 2009 |
| Class: 3A | | Round 1 | | Headland (6-4, 7-3) Straughn. Headland wins series (2-0) | | Round 2 | | Luverne (3-0, 13-1) Headland. Headland loses series (0-2) |
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| 2008 |
| Class: 3A | | Round 1 | | Headland (0-9, 10-6, 9-4) Catholic Montgomery. Headland wins series (2-1) | | Round 2 | | Headland (14-3, 0-10, 14-0) Leeds. Headland wins series (2-1) | | Round 3 | | Mobile Christian (5-4, 3-2) Headland. Headland loses series (0-2) |
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| 2007 |
| Class: 3A | | Round 1 | | Headland (11-4) Greensboro. | | Round 2 | | Gordo (13-1, 0-6, 11-1) Headland. Headland loses series (1-2) |
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| 2006 |
| Class: 3A | | Round 1 | | Headland (15-5) Pike County. | | Round 2 | | Alabama Christian (11-1, 6-2) Headland. Headland loses series (0-2) |
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| 2005 |
| Class: 3A | | Round 1 | | Springville (4-3) Headland. |
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| 2004 |
| Class: 4A | | Round 1 | | Trinity (8-6) Headland. |
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| 2003 |
| Class: 4A | | Round 1 | | Gulf Shores (4-1) Headland. |
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| 2002 |
| Class: 4A | | Round 1 | | Headland (10-5) Choctaw County. | | Round 2 | | UMS-Wright (8-0) Headland. |
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| 2001 |
| Class: 4A | | Round 1 | | Rehobeth (13-3) Headland. |
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| 1997 |
| Class: 3A | | Round 1 | | Gordo (9-4) Headland. |
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| 1995 |
| Class: 4A | | Round 1 | | Headland (4-0) Geneva. | | Round 2 | | Childersburg (13-10) Headland. |
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| 1994 |
| Class: 4A | | Round 1 | | Headland (8-4) Pike County. | | Round 2 | | Greensboro (10-1) Headland. |
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| 1993 |
| Class: 4A | | Round 1 | | Headland (8-6) Pike County. | | Round 2 | | Greensboro (3-2) Headland. |
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| 1992 |
| Class: 4A | | Round 1 | | Geneva (14-7) Headland. |
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| 1991 |
| Class: 4A | | Round 1 | | Headland (10-9) Ashford. | | Round 2 | | Headland () B.B. Comer. | | Round 3 | | Daphne (12-4) Headland. |
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| 1990 |
| Class: 4A | | Round 1 | | Headland (10-0) Ashford. | | Round 2 | | Headland (9-3) Oak Grove. | | Round 3 | | Tallassee (12-2) Headland. |
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| 1986 |
| Class: 3A | | Round 1 | | Headland (11-5) Holtville. | | Round 2 | | Headland (9-5) Washington County. | | Semi-finals | | Headland (7-4, 6-3) Weaver. Headland wins series (2-0) | | Finals | | Headland (4-11, 10-2, 3-2) West Limestone. Headland wins series (2-1) |
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| 1980 |
| Class: 2A | | Round 1 | | Headland () Straughn. | | Round 2 | | Headland () J.F. Shields. | | Semi-finals | | Headland (5-1, 1-2, 12-3) Holtville. Headland wins series (2-1) | | Finals | | West Blocton (4-5, 4-3, 8-5) Headland. Headland loses series (1-2) |
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| 1974 |
| Class: 1A/2A | | Round 1 | | Ariton (10-2) Headland. |
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