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| 2023 |
| Class: 5A Fast Pitch | | Area | | | | Rehobeth (16-1) Headland | | Regional Tournament | | | | Gulf Shores (15-0) Headland | | | | Holtville (14-2) Headland |
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| 2016 |
| Class: 4A Fast Pitch | | Area | | | | Headland () Straughn | | Regional Tournament | | | | Clarke County (7-0) Headland | | | | Headland (9-8) UMS-Wright | | | | Headland (5-4) Straughn | | | | Catholic Montgomery (5-4) Headland |
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| 2015 |
| Class: 4A Fast Pitch | | Area | | | | Headland () Straughn | | Regional Tournament | | | 5/8/2015 | Headland (7-2) St. James | | | 5/8/2015 | UMS-Wright (4-2) Headland | | | 5/9/2015 | Straughn (7-5) Headland |
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| 2014 |
| Class: 4A Fast Pitch | | Area | | | | Headland (10-0) Ashford | | Regional Tournament | | | | Headland (15--0) Monroe County | | | | Headland (4-1) UMS-Wright | | | | Alabama Christian (12-2) Headland | | | | Headland (2-0) UMS-Wright | | Championship Round | | | | Alexandria (6-5) Headland | | | | Headland (5-4) Elmore County | | | | Haleyville (11-4) Headland |
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| 2012 |
| Class: 4A Fast Pitch | | Area | | | | Headland (12-6) Ashford | | Regional Tournament | | | 5/11/2012 | Headland (4-0) Escambia County | | | 5/11/2012 | Alabama Christian (4-2) Headland | | | 5/12/2012 | Headland (3-1) Saraland | | | 5/12/2012 | Headland (4-0) Thomasville | | | 5/12/2012 | Headland (6-2) Ashford | | | 5/12/2012 | Alabama Christian (8-1) Headland | | Championship Round | | | 5/18/2012 | Cherokee County (9-2) Headland | | | 5/18/2012 | Headland (9-5) Wilson | | | 5/19/2012 | Bibb County (5-3) Headland |
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| 2011 |
| Class: 4A Fast Pitch | | Area | | | | Straughn (8-4) Headland | | Regional Tournament | | | 5/13/2011 | Headland (7-0) Thomasville | | | 5/13/2011 | Alabama Christian (12-7) Headland | | | 5/13/2011 | Jackson (4-2) Headland |
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| 2010 |
| Class: 3A Fast Pitch | | Area | | | | Headland (13-3) Abbeville | | Regional Tournament | | | 5/7/2010 | Luverne (5-4) Headland | | | 5/7/2010 | Headland (3-1) T.R. Miller | | | 5/7/2010 | Headland (5-4) Geneva | | | 5/8/2010 | Headland (10-0) Slocomb | | | 5/8/2010 | Headland (4-0) Luverne | | | 5/8/2010 | Straughn (3-0) Headland | | Championship Round | | | 5/14/2010 | Winfield (7-4) Headland | | | 5/14/2010 | Elkmont (4-2) Headland |
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| 2009 |
| Class: 3A Fast Pitch | | Area | | | | Headland (2-1) Abbeville | | Regional Tournament | | | 5/8/2009 | Headland (4-1) T.R. Miller | | | 5/8/2009 | Straughn (3-0) Headland | | | 5/8/2009 | Luverne (9-0) Headland |
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| 2008 |
| Class: 3A Fast Pitch | | Sub State Round 1 | | | | Headland (3-4, 12-0, 4-3) Washington County. Headland wins series (2-1) | | Sub State Round 2 | | | 5/10/2008 | Leeds (9-0, 13-4) Headland. Headland loses series (0-2) |
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| 2007 |
| Class: 3A Fast Pitch | | Sub State Round 1 | | | | Catholic Montgomery (5-3, 5-4) Headland. Headland loses series (0-2) |
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| 2006 |
| Class: 3A Fast Pitch | | | | Straughn (1-6, 3-2, 4-3) Headland. Headland loses series (1-2) |
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| 2005 |
| Class: 3A Fast Pitch | | | 5/10/2005 | Headland (7-1, 14-2) Clarke County. Headland wins series (2-0) | | Sub State Round 2 | | | 5/14/2005 | Alabama Christian (3-2, 12-0) Headland. Headland loses series (0-2) |
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| 2004 |
| Class: 4A Fast Pitch | | Sub State Round 1 | | | 5/4/2004 | Headland (4-0, 8-1) Opp. Headland wins series (2-0) | | Sub State Round 2 | | | 5/8/2004 | Headland (5-4, 5-7, 5-4) Thomasville. Headland wins series (2-1) | | Championship Round | | | 5/13/2004 | Boaz (10-2) Headland | | | 5/13/2004 | Saks (6-1) Headland |
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| 2003 |
| Class: 4A Fast Pitch | | Sub State Round 2 | | | 5/10/2003 | Gulf Shores (18-0, 9-1) Headland. Headland loses series (0-2) |
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| 2002 |
| Class: 4A Fast Pitch | | | 5/11/2002 | Headland (7-9, 13-1, 5-0) T.R. Miller. Headland wins series (2-1) | | Championship Round | | | 5/16/2002 | Moody (17-3) Headland | | | 5/16/2002 | Wilson (7-2) Headland |
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| 2001 |
| Class: 4A/6A Slow Pitch | | Sub State Round 2 | | | 5/15/2001 | Headland (12-0, 17-7) Blount. Headland wins series (2-0) | | Championship Round | | | 5/18/2001 | Headland (7-6) Jacksonville | | | 5/18/2001 | Cullman (13-0) Headland | | | 5/18/2001 | Etowah (7-5) Headland |
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| 2000 |
| Class: 4A Slow Pitch | | Sub State Round 2 | | | 5/16/2000 | Headland (5-2, 17-2) Lanett. Headland wins series (2-0) | | Championship Round | | | 5/19/2000 | Hokes Bluff (14-4) Headland | | | 5/19/2000 | Rehobeth (15-8) Headland |
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| 1999 |
| Class: 4A Slow Pitch | | | 5/14/1999 | Headland (9-0) Elmore County | | | 5/14/1999 | Headland (12-1) Fairview | | | 5/15/1999 | Geneva (12-4) Headland | | | 5/15/1999 | East Lawrence (10-6) Headland |
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