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| Rex Havoc | 96/05/24 | |
| Defeats E. Z. Ryder; vacant in 98/10 for failing to defend title. | ||
| Robby Royce | 96/11/07 | |
| Defeats Brian Jewel in tournament final. | ||
| Bobby Jay | 97/02/28 | |
| Stripped in 97/05 after missing a title defense. | ||
| Robby Royce [2] | 97/07/03 | |
| Defeats Buggsy Sluggliano in tournament final. | ||
| Brian Jewel | 97/07/31 | |
| Mike Stone | 97/08/28 | |
| Bobby Jay [2] | 97/09/11 | |
| Tom Steele | 97/09/25 | |
| Title is held up because of a controversial decision | ||
| Mike Stone [2] | 97/10/26 | |
| Wins a battle royal. | ||
| Brian Jewel [2] | 97/12/18 | |
| Vacat on 98/04/30 due to a shoulder injury. | ||
| Bobby Jay [3] | 98/05/09 | Winnipeg, MB |
| Defeats E.Z. Ryder. | ||
| E. Z. Ryder | 98/05/22 | Seven Oaks, MB |
| Crusher Carlsen | 98/05/28 | Elmwood, MB |
| Charley Hayes | 98/07/26 | Regina, SK |
| The Mercenary | 98/09/25 | Winnipeg, MB |
| Defeats Darren Daulton and Charley Hayes in a triangle match | ||
| Darren Dalton | 99/01/06 | Winnipeg, MB |
| Brian Jewel [2] | 99/02/13 | |
| Vacates in 99/08 due to shoulder injury. | ||
| Robby Royce [3] | 00/03/11 | Ft. Garry, MB |
| Darren Dalton [2] | 00/06/28 | Winnipeg, MB |
| Robby Royce [4] | 00/08/23 | Elmwood, MB |
| Paul Diamond | 00/10/28 | St. Boniface, MB |
| Robby Royce [5] | 01/03/09 | St. Boniface, MB |
| Ernie Todd | 01/06/17 | |
| Royce returns the belt to Todd since he also holds NWA North American Heavyweight title. | ||
| Gene Swan | 01/09/28 | St. Boniface, MB |
| Stripped on 02/01/06 when Swan leaves CWF. | ||
| Bobby Collins | 02/05/26 | St. Boniface, MB |
| Wins a battle royal. | ||
| Dick Walker | 02/09/08 | Winnipeg, MB |
| Defeats Collins and Baron Von Meaner in a 3-way match. | ||
| Brian Jewel [4] | 03/03/07 | Winnipeg, MB |
| Stripped on 03/07/10. | ||
| Kenny Omega | 03/12/27 | Winnipeg, MB |
| Defeats T.J. Bratt in a 4-man tournament final. | ||
| Zack Mercury | 04/01/31 | Winnipeg, MB |
| Gibby Guerro | 04/06/04 | St. Laurent, MB |
| Steve Jaworski | 04/10/15 | Winnipeg, MB |
| Wins a an 18-man battle royal. | ||
| Kerry Brown | 05/01/09 | Winnipeg, MB |
| The Mauler | 05/06/24 | Whale Mountain, QC |
| Kerry Brown [2] | 05/08/13 | |
| Awarded back when the Mauler does not defend the title in rematch within 30 days; CWF leaves NWA and becomes an AWA affiliate in 05/08. | ||
| Wavell Starr | 05/09/17 | Lebret, SK |
| J.T. Thorn | 05/01/21 | Crane River, MB |
| Sammy Savard | 06/02/27 | Manitoba * |
| Kerry Brown [3] | 06/03/25 | Winnipeg, MB |
| Stripped on 06/10/12. | ||
| Ryan Wood | 06/10/12 | |
| Defeats Drako and Stallion in a handicap match; declared vacant on 06/11/01 as a result of protest filed by Kerry Brown. | ||
| Ricky Fontaine | 07/01/29 | Ontario * |
| Defeats J.T. Thorn. | ||
| J.T. Thorn | 07/02/06 | Ontario * |
| Kwan Chang | 07/02/17 | Manitoba * |
| CWF leaves AWA in 07/04. | ||
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