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| 2024 |
| Class: 1A | | Round 1 | | Leroy () Billingsley. Leroy wins series (2-1) | | Round 2 | | Sweet Water () Leroy. Leroy loses series (1-2) |
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| 2023 |
| Class: 1A | | Round 1 | | Leroy (13-3, 16-0) Berry Fayette. Leroy wins series (2-0) | | Round 2 | | Leroy (21-6, 11-1) Red Level. Leroy wins series (2-0) | | Round 3 | | Billingsley (6-1, 5-8, 4-3) Leroy. Leroy loses series (1-2) |
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| 2022 |
| Class: 2A | | Round 1 | | Leroy (8-0, 15-0) Highland Home. Leroy wins series (2-0) | | Round 2 | | Vincent (12-16, 2-1, 13-12) Leroy. Leroy loses series (1-2) |
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| 2021 |
| Class: 2A | | Round 1 | | Leroy (12-2, 15-0) Geneva County. Leroy wins series (2-0) | | Round 2 | | Ranburne (7-0, 2-5, 10-0) Leroy. Leroy loses series (1-2) |
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| 2019 |
| Class: 2A | | Round 1 | | Leroy (5-4, 4-1) J.U. Blacksher. | | Round 2 | | Leroy (1-4, 13-0, 9-7) Ranburne. | | Round 3 | | G.W. Long (5-4, 8-2) Leroy. |
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| 2018 |
| Class: 2A | | Round 1 | | Leroy (11-1, 16-0) Geneva County. | | Round 2 | | J.U. Blacksher (5-0, 0-6, 4-3) Leroy. |
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| 2017 |
| Class: 2A | | Round 1 | | Leroy (12-3, 13-1) Ariton. Leroy wins series (2-0) | | Round 2 | | Leroy (18-2, 11-1) Elba. Leroy wins series (2-0) | | Round 3 | | Leroy (7-4, 7-2) St. Lukes. Leroy wins series (2-0) | | Semi-finals | | G.W. Long (8-0, 6-0) Leroy. Leroy loses series (0-2) |
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| 2014 |
| Class: 2A | | Round 1 | | Leroy (4-1, 3-1) Sweet Water. Leroy wins series (2-0) | | Round 2 | | Mobile Christian (1-11, 6-3, 5-2) Leroy. Leroy loses series (1-2) |
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| 2012 |
| Class: 2A | | Round 1 | | Leroy (15-2, 18-1) Goshen. Leroy wins series (2-0) | | Round 2 | | Leroy (12-2, 18-0) Millry. Leroy wins series (2-0) | | Round 3 | | Leroy (3-0, 3-4, 7-0) Thorsby. Leroy wins series (2-1) | | Semi-finals | | Leroy (1-2, 2-1, 16-6) Flomaton. Leroy wins series (2-1) | | Finals | | Mars Hill (5-0, 3-6, 7-1) Leroy. Leroy loses series (1-2) |
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| 2011 |
| Class: 2A | | Round 1 | | Leroy (18-0, 20-0) Goshen. Leroy wins series (2-0) | | Round 2 | | Leroy (12-2, 12-1) Millry. Leroy wins series (2-0) | | Round 3 | | Leroy (15-5, 7-3) Mobile Christian. Leroy wins series (2-0) | | Semi-finals | | Leroy (19-14, 6-3) Thorsby. Leroy wins series (2-0) | | Finals | | American Christian (1-11, 10-5, 11-10) Leroy. Leroy loses series (1-2) |
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| 2010 |
| Class: 2A | | Round 1 | | Leroy (11-1, 1-17, 11-0) Houston Academy. Leroy wins series (2-0) | | Round 2 | | Leroy (2-3, 9-3, 5-3) G.W. Long. Leroy wins series (2-1) | | Round 3 | | Leroy (18-0, 15-2) Reeltown. Leroy wins series (2-0) | | Semi-finals | | Leroy (11-9, 9-3) Mobile Christian. Leroy wins series (2-0) | | Finals | | Mars Hill (5-4, 6-1) Leroy. Leroy loses series (0-2) |
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| 2009 |
| Class: 2A | | Round 1 | | Leroy (14-4, 7-4) Houston Academy. Leroy wins series (2-0) | | Round 2 | | Leroy (5-3, 17-5) G.W. Long. Leroy wins series (2-0) | | Round 3 | | Leroy (9-1, 18-1) Excel. Leroy wins series (2-0) | | Semi-finals | | American Christian (1-0, 11-5) Leroy. Leroy loses series (0-2) |
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| 2008 |
| Class: 2A | | Round 1 | | Leroy (10-0, 17-7) Red Level. Leroy wins series (2-0) | | Round 2 | | Leroy (8-5, 12-1) G.W. Long. Leroy wins series (2-0) | | Round 3 | | Leroy (2-12, 12-7, 11-8) Wicksburg. Leroy wins series (2-1) | | Semi-finals | | Leroy (8-7, 1-10, 20-5) American Christian. Leroy wins series (2-1) | | Finals | | Leroy (6-7, 17-7, 16-4, ) Mars Hill. Leroy wins series (2-1) |
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| 2007 |
| Class: 2A | | Round 1 | | Leroy (16-6) Reeltown. | | Round 2 | | Leroy (13-3, 10-3) Houston County. Leroy wins series (2-0) | | Round 3 | | Leroy (16-5, 10-5) G.W. Long. Leroy wins series (2-0) | | Semi-finals | | Leroy (15-10, 10-8) Houston Academy. Leroy wins series (2-0) | | Finals | | Leroy (8-0, 3-1) Hatton. Leroy wins series (2-0) |
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| 2006 |
| Class: 2A | | Round 1 | | Leroy (15-0) Randolph County. | | Round 2 | | Ranburne (2-3, 2-1, 9-8) Leroy. Leroy loses series (1-2) |
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| 2005 |
| Class: 2A | | Round 1 | | Leroy (9-3) Clay County. | | Round 2 | | Leroy (10-1, 9-0) Horseshoe Bend. Leroy wins series (2-0) | | Round 3 | | Leroy (4-1, 4-2) Excel. Leroy wins series (2-0) | | Semi-finals | | G.W. Long (2-4, 7-1, 8-5) Leroy. Leroy loses series (1-2) |
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| 2004 |
| Class: 2A | | Round 1 | | Leroy (12-4) Luverne. | | Round 2 | | Gordo (5-4) Leroy. |
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| 2003 |
| Class: 2A | | Round 1 | | Leroy (9-5) G.W. Long. | | Round 2 | | Geneva County (8-7) Leroy. |
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| 2002 |
| Class: 2A | | Round 1 | | Leroy (5-4) Wicksburg. | | Round 2 | | Houston Academy (4-3) Leroy. |
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| 2001 |
| Class: 2A | | Round 1 | | Leroy (13-3) Red Level. | | Round 2 | | Leroy (8-0) Marbury. | | Round 3 | | Leroy (10-1, 3-5, 13-2) Geneva County. Leroy wins series (2-1) | | Semi-finals | | Leroy (3-2, 2-1) Houston Academy. Leroy wins series (2-0) | | Finals | | Leroy (11-0, 6-2) Gordo. Leroy wins series (2-0) |
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| 2000 |
| Class: 3A | | Round 1 | | Leroy (17-0) Goshen. | | Round 2 | | Briarwood (11-8) Leroy. |
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| 1999 |
| Class: 3A | | Round 1 | | Leroy (10-2) Luverne. | | Round 2 | | Leroy (4-0) Vincent. | | Round 3 | | UMS-Wright (3-2) Leroy. |
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| 1998 |
| Class: 2A | | Round 1 | | Leroy (8-6) Alabama Christian. | | Round 2 | | G.W. Long (5-2) Leroy. |
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| 1997 |
| Class: 2A | | Round 1 | | Leroy (7-6) Geneva County. | | Round 2 | | G.W. Long (12-3) Leroy. |
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| 1996 |
| Class: 2A | | Round 1 | | Leroy (12-9) Geneva County. | | Round 2 | | Leroy (3-0) Straughn. | | Round 3 | | Flomaton (8-5) Leroy. |
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| 1995 |
| Class: 2A | | Round 1 | | Excel (1-0) Leroy. |
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| 1994 |
| Class: 2A | | Round 1 | | Flomaton (8-7) Leroy. |
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| 1993 |
| Class: 2A | | Round 1 | | Leroy (12-5) Excel. | | Round 2 | | Leroy (16-6) Goshen. | | Round 3 | | Alabama Christian (3-2) Leroy. |
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| 1990 |
| Class: 2A | | Round 1 | | J.F. Shields (11-0) Leroy. |
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| 1989 |
| Class: 2A | | Round 1 | | Flomaton (5-0) Leroy. |
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| 1988 |
| Class: 2A | | Round 1 | | Flomaton (6-0) Leroy. |
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| 1954 |
| Class: A | | Round 1 | | Leroy (5-4) Baldwin County. | | Round 2 | | Leroy (7-4) Ashford. | | Round 3 | | Sidney Lanier (4-0) Leroy. |
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