| Loser to a pair | 15 |
| Loser to a tortoise | 19 |
| Loser to a trey | 15 |
| Loser to A.L. in 1864 | 21 |
| Loser to Affirmed in all three Triple Crown races | 49 |
| Loser to Al Pacino for Best Actor of 1992 | 41 |
| Loser to Ali | 12 |
| Loser to Apollo Creed in their first bout | 41 |
| Loser to Audrey for the 1953 Best Actress Oscar | 47 |
| Loser to Barack | 15 |
| Loser to Björn in the 1976 Wimbledon final | 45 |
| Loser to Bon Homme Richard: 1779 | 32 |
| Loser to Botvinnik in 1961 | 26 |
| Loser to Braddock | 17 |
| Loser to Braddock, 1935 | 23 |
| Loser to Braddock: 1935 | 23 |
| Loser to Buchanan: 1856 | 23 |
| Loser to Bush | 13 |
| Loser to Bush in 1988 | 21 |
| Loser to Bush in 2000 | 21 |
| Loser to Cassius Clay | 21 |
| Loser to Chamorro in 1990 | 25 |
| Loser to Clay in 1964 | 21 |
| Loser to Clay: 1964 | 19 |
| Loser to Cleveland in 1884 | 26 |
| Loser to Cleveland: 1884 | 24 |
| Loser to Clinton | 16 |
| Loser to Clinton in '96 | 27 |
| Loser to Clinton in 1996 | 24 |
| Loser to Cromwell: 1651 | 23 |
| Loser to D.D.E. | 15 |
| Loser to D.D.E. twice | 21 |
| Loser to DDE | 12 |
| Loser to Dempsey, 9/14/23 | 25 |
| Loser to Dwight | 15 |
| Loser to Dwight in the 50's | 31 |
| Loser to Dwight, twice | 22 |
| Loser to Eisenhower: 1952 and 1956 | 34 |
| Loser to F.D.R. | 15 |
| Loser to F.D.R.: 1936 | 21 |
| Loser to FDR in 1944 | 20 |
| Loser to Fischer in Reykjavik | 29 |
| Loser to Franklin | 17 |
| Loser to Franklin in 1936 | 25 |
| Loser to Franklin: 1936 | 23 |
| Loser to Frazier | 16 |
| Loser to Gans | 13 |
| Loser to Gans in 1902 | 21 |
| Loser to Gans: 1902 bout | 24 |
| Loser to Gen. Wolfe | 19 |
| Loser to Ghana in the 2010 World Cup | 36 |
| Loser to Grant | 14 |
| Loser to Grant: 1868 | 20 |
| Loser to Grant: 1872 | 20 |
| Loser to H.C.H. | 15 |
| Loser to H.C.H. in 1928 | 23 |
| Loser to H.C.H.: 1928 | 21 |
| Loser to H.S.T. | 15 |
| Loser to Happy Feet at the 2007 Oscars | 38 |
| Loser to Harding in 1920 | 24 |
| Loser to Herbert Hoover | 23 |
| Loser to Holmes | 15 |
| Loser to Holmes: June 11, 1982 | 30 |
| Loser to Hoover | 15 |
| Loser to Hoover: 1928 | 21 |
| Loser to Ike | 12 |
| Loser to Israel's Barak in 1999 | 35 |
| Loser to J.F.K. | 15 |
| Loser to Joe Louis in 1946 | 26 |
| Loser to Joe Louis: 1941 | 24 |
| Loser to Joe Louis: Sept. 1939 | 30 |
| Loser to Johnson | 16 |
| Loser to King in 1973 | 21 |
| Loser to King in tennis's "Battle of the Sexes" | 61 |
| Loser to King in the "Battle of the Sexes" tennis match | 65 |
| Loser to Leonard in 1980 | 24 |
| Loser to Lewis | 14 |
| Loser to Louis: 1941 | 20 |
| Loser to Louis: 1946 | 20 |
| Loser to Louis: Aug. 30, 1937 | 29 |
| Loser to Louis: Sept. 1939 | 26 |
| Loser to Louis: Sept. 29, 1941 | 30 |
| Loser to Lyndon: 1964 | 21 |
| Loser to Madison: 1812 | 22 |
| Loser to Mondale | 16 |
| Loser to Nastase at the 1972 U.S. Open finals | 45 |
| Loser to Norton, 1973 | 21 |
| Loser to Obama in 2004 | 22 |
| Loser to paper | 14 |
| Loser to paper and winner over scissors | 39 |
| Loser to Penn State: 1982 Sugar Bowl | 36 |
| Loser to Pierce in 1852 | 23 |
| Loser to Pierce: 1852 | 21 |
| Loser to R.B.H.: 1876 | 21 |
| Loser to R.M.N. | 15 |
| Loser to R.M.N. in '68 | 26 |
| Loser to R.M.N. in 1972 | 23 |
| Loser to R.M.N., 1968 | 21 |
| Loser to R.M.N.: 1968 | 21 |
| Loser to R.M.N.: 1972 | 21 |