| Regional Tournament History |
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| 2024 |
| Class: 1A Area: 5 | | Area | Calhoun 47-38 Ellwood Christian | | Area | Calhoun 57-56 Autaugaville | | Region C Championship | | Sub-Regional | Calhoun - Berry Fayette | | Regional | Calhoun 45-34 Billingsley | | Regional Finals | Calhoun 28-51 Keith |
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| 2023 |
| Class: 1A Area: 5 | | Area | Calhoun 47-26 Elwood Christian | | Area | Calhoun 51-52 Autaugaville | | Region C Championship | | Sub-Regional | Calhoun 24-58 Loachapoka |
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| 2022 |
| Class: 2A Area: 5 | | Area | Calhoun 37-36 Highland Home | | Area | Calhoun 41-51 Luverne | | Region S Championship | | Sub-Regional | Calhoun 48-52 Isabella |
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| 2021 |
| Class: 2A Area: 5 | | Area | Calhoun 37-34 Highland Home | | Area | Calhoun 28-43 Luverne | | Region S Championship | | Sub-Regional | Calhoun 47-48 Thorsby |
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| 2020 |
| Class: 2A Area: 6 | | Area | Calhoun 34-40 Luverne |
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| 2019 |
| Class: 2A Area: 6 | | Area | Calhoun 41-31 Luverne | | Area | Calhoun 33-56 Central Hayneville | | Region S Championship | | Sub-Regional | Calhoun 38-47 R.C. Hatch |
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| 2018 |
| Class: 2A Area: 6 | | Area | Calhoun 41-53 Luverne |
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| 2017 |
| Class: 2A Area: 6 | | Area | Calhoun 47-49 Goshen |
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| 2016 |
| Class: 2A Area: 6 | | Area | Calhoun 68-43 Highland Home | | Area | Calhoun 69-51 Central Hayneville | | Region C Championship | | Sub-Regional | Calhoun 62-44 Southern Choctaw | | Regional | Calhoun 26-38 R.C. Hatch |
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| 2015 |
| Class: 2A Area: 6 | | Area | Calhoun 0-0 Central Hayneville | | Area | Calhoun 34-31 Luverne | | Region Championship | | Sub-Regional | Calhoun 44-35 Washington County | | Regional | Calhoun 39-46 Lanett |
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| 2014 |
| Class: 2A Area: 6 | | Area | Calhoun 44-47 Central Hayneville |
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| 2013 |
| Class: 2A Area: 6 | | Area | Calhoun 49-43 Luverne | | Area | Calhoun 39-41 Central Hayneville | | Region C Championship | | Sub-Regional | Calhoun 21-57 Prattville Christian |
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| 2012 |
| Class: 2A Area: 5 | | Area | Calhoun 54-40 Highland Home | | Area | Calhoun 48-61 Central Hayneville | | Region C Championship | | Sub-Regional | Calhoun 32-55 Lanett |
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| 2011 |
| Class: 2A Area: 5 | | Area | Calhoun 48-36 Central Hayneville | | Area | Calhoun 48-39 Goshen | | Region C Championship | | Sub-Regional | Calhoun 36-50 Lanett |
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| 2010 |
| Class: 3A Area: 3 | | Area | Calhoun 26-24 Straughn | | Area | Calhoun 41-49 Central Hayneville | | Region S Championship | | Sub-Regional | Calhoun 38-65 T.R. Miller |
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| 2009 |
| Class: 3A Area: 3 | | Area | Calhoun 47-39 Central Hayneville | | Area | Calhoun 42-32 Straughn | | Region S Championship | | Sub-Regional | Calhoun 33-40 Bayside Academy |
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| 2008 |
| Class: 3A Area: 2 | | Area | Calhoun 50-27 Pike County | | Area | Calhoun 61-44 Straughn | | Region S Championship | | Sub-Regional | Calhoun 69-39 Washington County | | Regional | Calhoun 56-62 Geneva |
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| 2007 |
| Class: 3A Area: 2 | | Area | Calhoun 55-31 Elba | | Area | Calhoun 49-36 Straughn | | Region S Championship | | Sub-Regional | Calhoun 72-55 Clarke County | | Regional | Calhoun 56-51 LaFayette | | Regional Finals | Calhoun 54-56 Washington County |
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| 2006 |
| Class: 3A Area: 3 | | Area | Calhoun 50-68 Barbour County |
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| 2005 |
| Class: 3A Area: 3 | | Area | Calhoun 53-33 Pike County | | Area | Calhoun 33-72 Barbour County | | Region SE Championship | | Sub-Regional | Calhoun 35-68 Abbeville |
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| 2004 |
| Class: 3A Area: 3 | | Area | Calhoun 31-36 Central Hayneville |
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| 2003 |
| Class: 3A Area: 3 | | Area | Calhoun 58-43 Pike County | | Area | Calhoun 47-80 Barbour County | | Region SE Championship | | Sub-Regional | Calhoun 38-64 Abbeville |
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| 2002 |
| Class: 3A Area: 2 | | Area | Calhoun 51-49 Elba | | Area | Calhoun 47-42 Pike County | | Region SE Championship | | Sub-Regional | Calhoun 36-51 Alabama Christian |
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| 2001 |
| Class: 3A Area: 2 | | Area | Calhoun 0-0 Pike County | | Area | Calhoun 41-37 Elba | | Region SE Championship | | Sub-Regional | Calhoun 44-51 Alabama Christian |
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| 2000 |
| Class: 3A Area: 4 | | Area | Calhoun 0-0 Bye | | Area | Calhoun 70-36 Luverne | | Region SE Championship | | Sub-Regional | Calhoun 46-22 Elba | | Regional | Calhoun 50-55 Montgomery Academy |
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| 1999 |
| Class: 3A Area: 4 | | Area | Calhoun 0-0 | | Area | Calhoun 66-38 Goshen | | Region SE Championship | | Sub-Regional | Calhoun 81-65 Clayton | | Regional | Calhoun 49-70 Trinity |
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| 1998 |
| Class: 3A Area: 4 | | Area | Calhoun 50-77 Trinity |
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| 1997 |
| Class: 3A Area: 4 | | Area | Calhoun 57-48 St. James | | Area | Calhoun 53-61 Trinity | | Region SE Championship | | Sub-Regional | Calhoun 43-52 Headland |
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| 1996 |
| Class: 3A Area: 5 | | Area | Calhoun 46-61 St. James |
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| 1995 |
| Class: 3A | | Sub-Regional | Calhoun 57-82 St. Pauls |
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| 1994 |
| Class: 4A Area: 2 | | Area | Calhoun 0-0 | | Area | Calhoun 29-58 Clarke County | | Region S Championship | | Sub-Regional | Calhoun 60-69 Opp |
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| 1993 |
| Class: 4A Area: 2 | | Area | Calhoun 49-56 Clarke County | | Area | Calhoun 52-28 Central Hayneville | | Region S1 Championship | | Sub-State | Calhoun 21-32 T.R. Miller |
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| 1991 |
| Class: 4A Area: 2 | | Area | Calhoun 0-0 Clarke County |
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| 1990 |
| Class: 4A Area: 2 | | Area | Calhoun 0-0 Southside Selma | | Area | Calhoun 0-0 Bye | | Region S1 Championship | | Sub-State | Calhoun 38-35 T.R. Miller | | Sub-State Finals | Calhoun 46-63 Dale County |
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| 1989 |
| Class: 4A Area: 2 | | Area | Calhoun 0-0 Southside Selma | | Area | Calhoun 0-0 | | Region S1 Championship | | Sub-State | Calhoun 35-72 Clarke County |
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| 1981 |
| Class: 2A Area: 5 | | 1 | Calhoun 60-30 Catholic Montgomery | | Semi | Calhoun 37-49 Autaugaville |
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