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| 2021 |
| Class: 3A | | Round 1 | | Hale County (5-3, 13-3) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2019 |
| Class: 3A | | Round 1 | | Montgomery Academy (11-0, 1-3, 3-0) Dadeville. | | Round 2 | | Providence Christian (14-0, 13-3) Montgomery Academy. |
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| 2018 |
| Class: 3A | | Round 1 | | Montgomery Academy (12-2, 10-0) Indian Springs. | | Round 2 | | Gordo (11-1, 10-0) Montgomery Academy. |
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| 2017 |
| Class: 3A | | Round 1 | | Montgomery Academy (6-1, 15-7) Excel. Montgomery Academy wins series (2-0) | | Round 2 | | American Christian (4-0, 5-0) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2016 |
| Class: 3A | | Round 1 | | Montgomery Academy (13-3, 10-7) Hale County. Montgomery Academy wins series (2-0) | | Round 2 | | American Christian (2-1, 8-1) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2015 |
| Class: 3A | | Round 1 | | American Christian (5-7, 10-2, 5-1) Montgomery Academy. Montgomery Academy loses series (1-2) |
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| 2014 |
| Class: 2A | | Round 1 | | Hale County (8-0, 8-0) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2013 |
| Class: 2A | | Round 1 | | Montgomery Academy (0-6, 11-4, 11-10) Hale County. Montgomery Academy wins series (2-1) | | Round 2 | | Prattville Christian (9-4, 4-3) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2007 |
| Class: 3A | | Round 1 | | Montgomery Academy (11-0) Straughn. | | Round 2 | | Washington County (9-2, 9-5) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2006 |
| Class: 3A | | Round 1 | | Montgomery Academy (9-1) Sumiton Christian. | | Round 2 | | Montgomery Academy (10-4, 16-4) Slocomb. Montgomery Academy wins series (2-0) | | Round 3 | | Montgomery Academy (8-7, 9-3) T.R. Miller. Montgomery Academy wins series (2-0) | | Semi-finals | | Montgomery Academy (4-3, 4-0) Dadeville. Montgomery Academy wins series (2-0) | | Finals | | Hokes Bluff (5-1, 1-8, 14-4) Montgomery Academy. Montgomery Academy loses series (1-2) |
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| 2005 |
| Class: 3A | | Round 1 | | Montgomery Academy (5-3) Dadeville. | | Round 2 | | Montgomery Academy (14-4, 6-1) Sumiton Christian. Montgomery Academy wins series (2-0) | | Round 3 | | Montgomery Academy (8-2, 3-0) T.R. Miller. Montgomery Academy wins series (2-0) | | Semi-finals | | Montgomery Academy (5-0, 3-6, 15-1) Springville. Montgomery Academy wins series (2-1) | | Finals | | Hokes Bluff (3-6, 10-0, 9-1) Montgomery Academy. Montgomery Academy loses series (1-2) |
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| 2004 |
| Class: 3A | | Round 1 | | Montgomery Academy (28-1) Francis Marion. | | Round 2 | | Montgomery Academy (6-4) T.R. Miller. | | Round 3 | | Montgomery Academy (6-1, 4-1) Straughn. Montgomery Academy wins series (2-0) | | Semi-finals | | Alabama Christian (3-13, 7-6, 8-3) Montgomery Academy. Montgomery Academy loses series (1-2) |
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| 2003 |
| Class: 3A | | Round 1 | | Montgomery Academy (11-5) Clarke County. | | Round 2 | | Montgomery Academy (10-5) Oak Grove. | | Round 3 | | Montgomery Academy (11-5, 7-2) Holtville. Montgomery Academy wins series (2-0) | | Semi-finals | | Montgomery Academy (5-2, 5-0) Dadeville. Montgomery Academy wins series (2-0) | | Finals | | Ashville (5-2, 8-2) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2002 |
| Class: 3A | | Round 1 | | Montgomery Academy (14-8) W.S. Neal. | | Round 2 | | Montgomery Academy (11-0) Northside. | | Round 3 | | Ashville (5-2, 12-2) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 2001 |
| Class: 3A | | Round 1 | | Northside (2-1) Montgomery Academy. |
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| 2000 |
| Class: 3A | | Round 1 | | Elba (8-7) Montgomery Academy. |
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| 1997 |
| Class: 2A | | Round 1 | | Montgomery Academy (22-0) J.F. Shields. | | Round 2 | | Montgomery Academy (7-2) Straughn. | | Round 3 | | Flomaton (7-2) Montgomery Academy. |
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| 1994 |
| Class: 1A | | Round 1 | | Montgomery Academy () Bye. | | Round 2 | | Montgomery Academy (8-5) Millry. | | Round 3 | | Houston Academy (9-3) Montgomery Academy. |
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| 1993 |
| Class: 1A | | Round 1 | | Montgomery Academy (19-5) Beulah. | | Round 2 | | Frisco City (12-1) Montgomery Academy. |
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| 1992 |
| Class: 1A | | Round 1 | | Montgomery Academy (8-2) Marbury. | | Round 2 | | Montgomery Academy (11-1) Frisco City. | | Round 3 | | G.W. Long (12-0) Montgomery Academy. |
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| 1991 |
| Class: 1A | | Round 1 | | Marbury (8-6) Montgomery Academy. |
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| 1982 |
| Class: 1A | | Round 1 | | Montgomery Academy (15-3) Thorsby. | | Round 2 | | Montgomery Academy (7-1) Clayton. |
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| 1981 |
| Class: 1A | | Round 1 | | Montgomery Academy (9-0) Thorsby. | | Round 2 | | Montgomery Academy (11-1) Mt. Olive. | | Semi-finals | | Montgomery Academy (7-10, 9-3, 8-6) Fruitdale. Montgomery Academy wins series (2-1) | | Finals | | Montgomery Academy (4-0, 7-4) Coosa County. Montgomery Academy wins series (2-0) |
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| 1980 |
| Class: 1A | | Round 1 | | Montgomery Academy (5-4) Billingsley. | | Round 2 | | Montgomery Academy (7-4) Rebecca Comer. | | Semi-finals | | Sweet Water (1-0, 4-0) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 1979 |
| Class: 1A | | Round 1 | | Montgomery Academy () Billingsley. | | Round 2 | | Montgomery Academy (6-4) Ariton. | | Semi-finals | | Sweet Water (10-0, 6-4) Montgomery Academy. Montgomery Academy loses series (0-2) |
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| 1977 |
| Class: 1A | | Round 1 | | Montgomery Academy (2-1) Millry. | | Round 2 | | Montgomery Academy (6-5) Isabella. | | Semi-finals | | Montgomery Academy (20-4, 9-2) Marbury. Montgomery Academy wins series (2-0) | | Finals | | Mars Hill (4-3, 6-3) Montgomery Academy. Montgomery Academy loses series (0-2) |
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