| Past Masters Winter Garden Lodge No. 165 | |||||||
| 1907 | Joseph Elwell * | 1937 | L. Frank Roper * | 1967 | D. E. Duppenthaler * | 1997 | Frankie D. Colbum |
| 1908 | Charlies H. Tilden * | 1938 | R. M. Morris * | 1968 | Jonathan N. Branch * | 1998 | Thomas B. Jenkins |
| 1909 | Charlies H. Tilden * | 1939 | C. L. Stanford * | 1969 | Charles W. Irrgang III * | 1999 | Rodney C. Hollis * |
| 1910 | Georga T. Smith * | 1940 | E. W. Reaves * | 1970 | Jack L. Quesinberry PDDGM * | 2000 | Lawrence A. Drake Jr. |
| 1911 | J.E. Petris * | 1941 | O. L. Sands PDDGM * | 1971 | Billy E. Peavey * | 2001 | Reid J. Revels |
| 1912 | W.T. Hickman * | 1942 | O. L. Sands PDDGM * | 1972 | J. Gordon Russ * | 2002 | Robert E. Burke Jr. * |
| 1913 | Joseph Elwell * | 1943 | O. L. Sands PDDGM * | 1973 | Nial P. Handley * | 2003 | James A. Avera * |
| 1914 | J.E. Petris * | 1944 | E. W. Reaves * | 1974 | John Cook * | 2004 | J. Steven Teal PDDGM |
| 1915 | Roy R. Roper * | 1945 | Bruce N. Jones PDDGM * | 1975 | Galen Cline * | 2005 | Robert Whyte |
| 1916 | E. F. Niblact * | 1946 | Bruce N. Jones PDDGM * | 1976 | Walter P. Carreker + | 2006 | Barton ” Bart” A. Patria |
| 1917 | A. J. Willis * | 1947 | Robert H. Quesinberry * | 1977 | Herbert H. Blitch | 2007 | George ” Jabo” Pellam * |
| 1918 | Georga T. Smith * | 1948 | Harry M. Daniel * | 1978 | Zeb C. Peacock Jr. * | 2008 | Wilbur A. Smith III |
| 1919 | Louis D. Jones * | 1949 | M. G. Parramore PDDGM * | 1979 | Julian L. Revels * | 2009 | Scott Penvose |
| 1920 | Bert H. Roper * | 1950 | Ed C. Reaves * | 1980 | Gordon W. Giddens + | 2010 | Ken Lyons |
| 1921 | H G. Briley * | 1951 | R. F. Anderson * | 1981 | John H. Linebarier + | 2011 | Garland ” Gary” Story |
| 1922 | A. F. Landstreet * | 1952 | Roger B. Seidner * | 1982 | Carl A. Shepard * | 2012 | Michael Kilgore |
| 1923 | W. Fred Roper * | 1953 | J. M. Groover * | 1983 | Charles D. Counterman + | 2013 | Sly Cawley |
| 1924 | J. E. Clonts * | 1954 | L. E. Johnson * | 1984 | Bemard C. Williams * | 2014 | Jerry Clark, PDDGM |
| 1925 | Clarence Lau * | 1955 | Clyde E. Roberson * | 1985 | Robert A. Davis + * | 2015 | Francisco Lopez |
| 1926 | Waymon A. Wilkes * | 1956 | M. T. Monor * | 1986 | Paul W. Tnsley | 2016 | J. Mark Kirkley |
| 1927 | L. H. King* | 1957 | W. H. Hinson * | 1987 | George C. Woodward * | 2017 | Clawson Peacock |
| 1928 | L. H. King* | 1958 | L. G. Donahey * | 1988 | John W. Carrol + * | 2018 | Michael Kramer |
| 1929 | W. H. Hamage * | 1959 | W. D. Hartzog * | 1989 | L. Wade Rich | 2019 | David Barron |
| 1930 | Harry M. Smith * | 1960 | A. J. Thunell * | 1990 | Robert R. Jones | 2020 | Gil Alvarez |
| 1931 | H. C. Mink* | 1961 | Vard J. Hager * | 1991 | Paul O. Harvey | 2021 | Luis Oliveira |
| 1932 | Harry M. Smith * | 1962 | Charlies McMillian * | 1992 | Veryl M. Summerlin * | 2022 | Jose Morales |
| 1933 | Harry M. Smith * | 1963 | Clarenace E. Heidt * | 1993 | Darrell W. Clay | 2023 | Steve Dimond |
| 1934 | Waymon A. Wilkes * | 1964 | Harvey L. Davis * | 1994 | Charles F. Roper | ||
| 1935 | Thomas D. Mack * | 1965 | John H. Loucks * | 1995 | Arther F. Young Jr. | * | Deceased |
| 1936 | Charles Gregory * | 1966 | John V. Tyndal * | 1996 | Weldon L. Wichman | + | Demitted |