| 1908 | Mr. W. A. Anderson | Fannie Lewis #4 | Richmond |
| 1921 | Mr. J. W. Barnes | Martha #10 | Portsmouth |
| 1932 | Rev. S. S. Morris | Martha #10 | Portsmouth |
| 1938 | Mr. Warren W. Lee | Celestia #38 | Fredericksburg |
| 1942 | Mr. J. E. Fulford | Elizabeth #34 | Norfolk |
| 1944 | Mr. William C. Dudley | Success #85 | Salem |
| 1946 | Mr. C. V. Wilson | Goodwill #125 | Lynchburg |
| 1958 | Dr. W. L. Ransome | Hannah #26 | Richmond |
| 1974 | Mr. William Fox | Elizabeth Harris #86 | Richmond |
| 1974 | Rev. E. C. Kent | Carey Wheaton #204 | Mechanicsville |
| 1986 | Mr. Reginald W. Coles | Richmond #1 | Richmond |
| 1994 | Mr. Richard M. Fitzgerald | Elizabeth Harris #86 | Richmond |
| 2005 | Mr. Henry Barbour | Excelsior #82 | Norfolk |
| 2007 | Rev. Clarence E. Miller | Elizabeth Fragrant Rose #34 | Norfolk |
| 2007 | Mr. John N. Daughtry | Brighton Light #118 | Portsmouth |
| 2009 | Mr. Larry D. Christian | United #169 | New Kent |
| 2010 | Mr. Floyd Brown Sr. | Helena #110 | Disputanta |
| 2011 | Mr. Herman Eggleston, Jr. | Charlotte #147 | Keysville |
| 2012 | Mr. Garland Jones | Mary C. Stewart #128 | Richmond |
| 2013 | Mr. William Christian | Mary C. Stewart #128 | Richmond |
| 2014 | Mr. Johnnie Wiggins | Naomi #123 | Waverly |
| 2015 | Mr. Donald S. Wilson | Adah #20 | Norfolk |
| 2016 | Mr. William Steele | Star of Hope #164 | Petersburg |
| 2017 | Mr. Joseph Diggs, Sr. | Electa #7 | Petersburg |
