| Loser to Bush in 1988 | 21 |
| Loser to Bush | 13 |
| Loser to Buchanan: 1856 | 23 |
| Loser to Braddock: 1935 | 23 |
| Loser to Braddock, 1935 | 23 |
| Loser to Braddock | 17 |
| Loser to Botvinnik in 1961 | 26 |
| Loser to Bon Homme Richard: 1779 | 32 |
| Loser to Björn in the 1976 Wimbledon final | 45 |
| Loser to Barack | 15 |
| Loser to Audrey for the 1953 Best Actress Oscar | 47 |
| Loser to Apollo Creed in their first bout | 41 |
| Loser to Ali | 12 |
| Loser to Al Pacino for Best Actor of 1992 | 41 |
| Loser to Affirmed in all three Triple Crown races | 49 |
| Loser to A.L. in 1864 | 21 |
| Loser to a trey | 15 |
| Loser to a tortoise | 19 |
| Loser to a pair | 15 |
| Loser to "Mutiny on the Bounty" for Best Picture | 58 |
| Loser to "Chariots of Fire" for Best Picture | 54 |
| Loser to "Cabaret" for Best Musical | 45 |
| Loser to ''Million Dollar Baby'' for Best Picture | 65 |
| Loser of the "golden apples" race | 43 |
| Loser of the ''Fight of the Century'' | 53 |
| Loser of lore | 13 |
| Loser of friends | 16 |
| Loser of a race | 15 |
| Loser of a footrace with Hippomenes | 35 |
| Loser of a flock | 16 |
| Loser of a fabled race | 22 |
| Loser of 1992 | 13 |
| Loser of 1988 | 13 |
| Loser of 1948 | 13 |
| Loser of 1917 | 13 |
| Loser of 1588 | 13 |
| Loser in war, usually | 21 |
| Loser in the Seven Years' War: Abbr. | 40 |
| Loser in the first World Series, 1903 | 37 |
| Loser in the Battle of Bannockburn, 1314 | 40 |
| Loser in the 2000 headlines | 27 |
| Loser in the 1998 NBA finals | 28 |
| Loser in many product comparisons | 33 |
| Loser in Brown v. Board of Education | 36 |
| Loser in an upset | 17 |
| Loser in an fictional upset | 27 |
| Loser in a staring contest | 26 |
| Loser in a rout | 15 |
| Loser in a legendary upset | 26 |
| Loser in a fictional upset | 26 |
| Loser in a fabled upset | 23 |
| Loser in a fabled race | 22 |
| Loser in a fable | 16 |
| Loser in a casino | 17 |
| Loser in a 1962 showdown with J.F.K. | 36 |
| Loser in a '70s landslide | 29 |
| Loser in 1996 | 13 |
| Loser in 1988 | 13 |
| Loser in 1980 | 13 |
| Loser in 1972 | 13 |
| Loser in 1912 election | 22 |
| Loser in 1588 | 13 |
| Loser in 1066 | 13 |
| Loser in ''Cinderella Man'' | 43 |
| Loser at Waterloo | 17 |
| Loser at the dice table | 23 |
| Loser at the Battle of Châlons, A.D. 451 | 43 |
| Loser at sea in 1588 | 20 |
| Loser at Salamis and Plataea | 28 |
| Loser at Palo Alto: 1846 | 24 |
| Loser at Little Bighorn | 23 |
| Loser at Little Big Horn | 24 |
| Loser at Hastings | 17 |
| Loser at Gettysburg | 19 |
| Loser at Fredericksburg | 23 |
| Loser at El Alamein | 19 |
| Loser at Châlons-sur-Marne in 451 | 36 |
| Loser at Châlons in A.D. 451 | 31 |
| Loser at Appomattox | 19 |
| Loser at Antietam | 17 |
| Loser | 5 |
| Lose-weight-fast plan | 21 |
| Lose-weight schemes | 19 |
| Lose-lose situations | 20 |
| Lose-lose | 9 |
| Lose, slangily | 14 |
| Lose, old style | 15 |
| Lose, in sports headlines | 25 |
| Lose, in a way | 14 |
| Lose, in a Vegas game | 21 |
| Lose, as skin | 13 |
| Lose, as one's tail | 23 |
| Lose, as a tail | 15 |
| Lose, as a layer | 16 |
| Lose, as a big lead | 19 |
| Lose ___ cool | 13 |
| Lose ___ (slow down) | 20 |
| Lose zip | 8 |
| Lose zest | 9 |
| Lose yours and you're nuts | 30 |