| 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 |
| Loser to Reagan: 1970 | 21 |
| Loser to Reagan: 1984 | 21 |
| Loser to Richard in '68 | 27 |
| Loser to Richard: 1968 | 22 |
| Loser to Roosevelt | 18 |
| Loser to Roosevelt and Truman | 29 |
| Loser to Roosevelt in 1932 | 26 |
| Loser to Roosevelt: 1904 | 24 |
| Loser to S. Grant | 17 |
| Loser to Sheridan in the Shenandoah Valley | 42 |
| Loser to Sparta | 15 |
| Loser to Sparta in the Peloponnesian War | 40 |
| Loser to Spinks | 15 |
| Loser to St. George | 19 |
| Loser to Steven Soderbergh for Best Director of 2000 | 52 |
| Loser to Taft in 1908 | 21 |
| Loser to Taylor in 1848 | 23 |
| Loser to the Ottomans in 1711 | 29 |
| Loser to the tortoise | 21 |
| Loser to Truman | 15 |
| Loser to Truman: 1948 | 21 |
| Loser to U.S. in 1815 | 21 |
| Loser to U.S.G. | 15 |
| Loser to VHS | 12 |
| Loser to Wilson | 15 |
| Loser who's happy | 21 |
| Loser's "name" | 28 |
| Loser's catchphrase | 23 |
| Loser's catchword | 21 |
| Loser's concern | 19 |
| Loser's cry | 15 |
| Loser's demand | 18 |
| Loser's destination | 23 |
| Loser's eating | 18 |
| Loser's fare | 16 |
| Loser's food | 16 |
| Loser's holding | 19 |
| Loser's hoped-for path | 26 |
| Loser's impatient command | 29 |
| Loser's lament | 18 |