| 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 |
| Loser's lament? | 19 |
| Loser's look | 16 |
| Loser's metaphor | 20 |
| Loser's order, perhaps | 26 |
| Loser's place | 17 |
| Loser's place? | 18 |
| Loser's problem, perhaps | 28 |
| Loser's reaction | 20 |
| Loser's regimen | 19 |
| Loser's request | 19 |
| Loser's slip | 16 |
| Loser's target? | 19 |
| Loser's total in a shutout | 30 |
| Loser's unit | 16 |
| Loser's weepers | 19 |
| Loser's weepers? | 20 |
| Loser's whiny response | 26 |
| Loser's word | 16 |
| Loser's word? | 17 |
| Loser, proverbially | 19 |
| Loser, to Loos | 14 |
| Loser, with Bono, to Fabio, in a 1999 "Celebrity Deathmatch" episode | 78 |
| LoserÂ’s cry | 15 |
| Loserless outcomes | 18 |
| Losers | 6 |
| Losers at Indy? | 15 |
| Losers at Vicksburg | 19 |
| Losers in '72 series | 24 |
| Losers in a race | 16 |
| Losers in the Battle of Horseshoe Bend | 38 |
| Losers in the Punic Wars | 24 |
| Losers in W.W. II | 17 |
| Losers of Super Bowl I | 22 |
| Losers of the 1998 World Series | 31 |
| Losers of the 2006 NLCS | 23 |
| Losers of the Battle of Meloria, 1284 | 37 |
| Losers on "The Apprentice"? | 37 |
| Losers to Agamemnon | 19 |
| Losers to BOS in the 2010 NBA playoffs | 38 |
| Losers to Brian Boru in 1014 | 28 |
| Losers to Caesar | 16 |
| Losers to the 49ers in Super Bowl XXIII | 39 |
| Losers to the Rangers for the 1994 Stanley Cup | 46 |
| Losers to the Yankees in the 1998 Series | 40 |
| Losers with good attitudes | 26 |
| Losers' count | 17 |
| Losers' hangout? | 20 |
| Losers' imperative | 22 |
| Losers' song to referee | 27 |
| Losers, in an anti-drug campaign | 32 |
| Loses | 5 |
| Loses (to) | 10 |
| Loses a coat | 12 |
| Loses a coat, in a way | 22 |
| Loses a lap | 11 |
| Loses a lap? | 12 |
| Loses a liking for | 18 |
| Loses a showdown, e.g. | 22 |
| Loses a skin, say | 17 |
| Loses a stare-down | 18 |