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| 2023 |
| Class: 1A | | Round 1 | | Billingsley (5-0, 8-1) University Charter School. Billingsley wins series (2-0) | | Round 2 | | Billingsley (16-1, 7-2) Florala. Billingsley wins series (2-0) | | Round 3 | | Billingsley (6-1, 5-8, 4-3) Leroy. Billingsley wins series (2-1) | | Semi-finals | | Brantley (2-1, 6-1) Billingsley. Billingsley loses series (0-2) |
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| 2022 |
| Class: 1A | | Round 1 | | Brantley (16-2, 16-2) Billingsley. Billingsley loses series (0-2) |
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| 2019 |
| Class: 1A | | Round 1 | | Billingsley (8-1, 6-3) Isabella. | | Round 2 | | Brantley (11-5, 13-3) Billingsley. |
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| 2017 |
| Class: 2A | | Round 1 | | Phil Campbell (6-3, 16-4) Billingsley. Billingsley loses series (0-2) |
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| 2016 |
| Class: 1A | | Round 1 | | Billingsley (9-3, 14-8) Verbena. Billingsley wins series (2-0) | | Round 2 | | Maplesville (9-3, 13-0) Billingsley. Billingsley loses series (0-2) |
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| 2015 |
| Class: 1A | | Round 1 | | Billingsley (19-0, 15-0) Loachapoka. Billingsley wins series (2-0) | | Round 2 | | Billingsley (12-0, 3-4, 10-6) Verbena. Billingsley wins series (2-1) | | Round 3 | | Billingsley (2-6, 7-2, 6-2) Ragland. Billingsley wins series (2-1) | | Semi-finals | | Brantley (6-2, 6-1) Billingsley. Billingsley loses series (0-2) |
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| 2014 |
| Class: 1A | | Round 1 | | Billingsley (12-8, 11-4) Verbena. Billingsley wins series (2-0) | | Round 2 | | Maplesville (8-0, 16-2) Billingsley. Billingsley loses series (0-2) |
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| 2013 |
| Class: 1A | | Round 1 | | Billingsley (7-6, 12-2) Wadley. Billingsley wins series (2-0) | | Round 2 | | Maplesville (12-2, 5-4) Billingsley. Billingsley loses series (0-2) |
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| 2012 |
| Class: 2A | | Round 1 | | Reeltown (13-3, 6-1) Billingsley. Billingsley loses series (0-2) |
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| 2010 |
| Class: 1A | | Round 1 | | Holy Spirit (11-1, 20-0) Billingsley. Billingsley loses series (0-2) |
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| 2009 |
| Class: 1A | | Round 1 | | Holy Spirit (22-2, 13-2) Billingsley. Billingsley loses series (0-2) |
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| 2008 |
| Class: 1A | | Round 1 | | Billingsley (11-7, 10-5) Isablella. Billingsley wins series (2-0) | | Round 2 | | Sweet Water (16-3, 14-0) Billingsley. Billingsley loses series (0-2) |
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| 2007 |
| Class: 1A | | Round 1 | | Pleasant Home (8-4) Billingsley. |
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| 2005 |
| Class: 2A | | Round 1 | | Wicksburg (6-2) Billingsley. |
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| 2000 |
| Class: 1A | | Round 1 | | Billingsley (6-4) Isabella. | | Round 2 | | Florala (11-0) Billingsley. |
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| 1999 |
| Class: 1A | | Round 1 | | Billingsley (10-0) Fruitdale. | | Round 2 | | Billingsley (11-0) Wadley. | | Round 3 | | G.W. Long (12-1) Billingsley. |
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| 1998 |
| Class: 1A | | Round 1 | | Ariton (3-2) Billingsley. |
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| 1997 |
| Class: 1A | | Round 1 | | Billingsley (7-4) Fruitdale. | | Round 2 | | Ariton (15-6) Billingsley. |
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| 1996 |
| Class: 1A | | Round 1 | | Billingsley (8-3) McKenzie. | | Round 2 | | Billingsley (5-0) G.W. Long. | | Round 3 | | Sweet Water (5-4) Billingsley. |
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| 1995 |
| Class: 1A | | Round 1 | | Billingsley (11-4) Carrollton. | | Round 2 | | G.W. Long (14-1) Billingsley. |
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| 1994 |
| Class: 1A | | Round 1 | | Carrollton (9-3) Billingsley. |
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| 1992 |
| Class: 1A | | Round 1 | | Trinity (12-2) Billingsley. |
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| 1987 |
| Class: 1A | | Round 1 | | Maplesville (11-1) Billingsley. |
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| 1980 |
| Class: 1A | | Round 1 | | Montgomery Academy (5-4) Billingsley. |
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| 1979 |
| Class: 1A | | Round 1 | | Montgomery Academy () Billingsley. |
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| 1972 |
| Class: 1A/2A | | Round 1 | | Thomasville (10-0) Billingsley. |
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