Through the mid 1990s:
1922-1925: Johnny Bryan
1923-1927: Roy White
1926: Clifford Lemon
1929-1930: Walter Holmer
1930-1934: Paul Franklin
1937: John Bettridge
1937-1938: Ray Buivid
1939-1945: Bill Osmanski
1948-1949: Dick Flanagan
1951-1953; Bob Williams
1961-1966: Bill Wade
1981: John Roveto
1982-1988; Jim McMahon
1993-1996: Shane Matthews
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FB Bill Osmanski.
Osmanski wore #9 for the Bears between 1939-1943 and 1946-1947 (he missed 1944 and 1945 as a Marine serving in World War II). In 1941, he rushed 70 times for 371 yards and 4 TDs and led the NFL with an average of 5.3 yards per rush.
18 Chicago Bears players wore #29:
Bill McElwain, 1925
John Wallace, 1928
Joe Kopcha, 1929-1933
Gus Mastrogany, 1931
Russ Thompson, 1936-1939
Ed Kolman, 1940-1944
Douglas McEnulty, 1943-1944
Glenn Burgeis, 1945
John Hoffman, 1949-1956
McNeil Moore, 1954-1956
Glen Shaw, 1960
Ronnie Bull, 1962-1970
Bob Jeter, 1971-1972
Mike Morgan, 1978
Vaughn Lusby, 1980
Dennis Gentry, 1982-1992
Raymont Harris, 1994-1997
Frankie Smith, 1998-Present