| The Olympics' 1980 host and 1984 boycotter | 46 |
| The Olympics held in Antwerp | 28 |
| The Olympics are full of them | 29 |
| The Olympic rings, e.g. | 23 |
| The Olympic logo's five | 27 |
| The Olympic logo has five | 25 |
| The Olympic Australis, e.g. | 27 |
| The Olympic Australis and others | 32 |
| The Olympians overthrew them | 28 |
| The Olsens, e.g. | 16 |
| The olds | 8 |
| The oldest Simpson | 18 |
| The oldest of the Baldwin brothers | 34 |
| The oldest mutual auto insurance company in the U.S. | 52 |
| The oldest Huxtable | 19 |
| The oldest Brady kid | 20 |
| The oldest animated Simpson | 27 |
| The older of two catch players | 30 |
| The older it gets, the flatter it gets | 38 |
| The older Gershwin brother | 26 |
| The older Dumas | 15 |
| The olden days | 14 |
| The Olde Towne Team, by another name | 36 |
| The old-time photographer preferred the __ | 42 |
| The old ____ | 12 |
| The Old ___ Bucket (Indiana-Purdue trophy, slangily) | 52 |
| The old ___ (Ireland) | 21 |
| The Old ___ | 11 |
| The old you? | 12 |
| The old you | 11 |
| The Old World | 13 |
| The Old South | 13 |
| The old soft shoe? | 18 |
| The old soft shoe | 17 |
| The Old Sod | 11 |
| The Old Professor | 17 |
| The old one-two? | 16 |
| The old Omni, for one | 21 |
| The old noodle | 14 |
| The old nine-to-five | 20 |
| The old maxim about moss gathering? | 35 |
| The old man: Ger. | 17 |
| The old man's old man | 25 |
| The old man in "The Old Man and the Sea" | 50 |
| The old man | 11 |
| The old heave-ho | 16 |
| The old grind for two actresses and two authors | 47 |
| The old gray one ain't what she used to be | 46 |
| The Old Gray Mare for example | 30 |
| The old frontier you and I don't remember? | 46 |
| The old folks | 13 |
| The Old Curiosity, e.g. | 23 |
| The old country, etc. | 21 |
| The old college __ | 18 |
| The old college try | 19 |
| The old college cry | 19 |
| The old college cheer | 21 |
| The old Boston Garden, e.g. | 27 |
| The old bean | 12 |
| The old ball game? | 18 |
| The old ball and chain? | 23 |
| The old Atlantic Hwy. | 21 |
| The old "ould sod" | 28 |
| The olés are not for them | 28 |
| The Okefenokee and others | 25 |
| The oil spill, for BP | 21 |
| The oil in its liver is a source of omega-3 fatty acids | 55 |
| The Ohre, to Hans | 17 |
| The Ohio River forms its southern border | 40 |
| The Ohio R. forms its southern border | 37 |
| The Offspring "___ Life" | 34 |
| The office supply manager brought ... | 37 |
| The offense or the defense | 26 |
| The offense and the defense | 27 |
| The OED, e.g. | 13 |
| The Oder, to Czechs | 19 |
| The Oder, to a Czech | 20 |
| The odds are against them | 25 |
| The odds | 8 |
| The oceanographer started ... | 29 |
| The ocean's B-team? | 23 |
| The Ocean State | 15 |
| The ocean | 9 |
| The obverse of a coin | 21 |
| The obstetrician had ___ | 24 |
| The oboist makes his a double | 29 |
| The object yonder | 17 |
| The object at hand | 18 |
| The obelisk on the National Mall, e.g. | 38 |
| The Obamas' degs. | 21 |
| The Obamas' Bo, for one | 27 |
| The Obamacare rollout, e.g. | 27 |
| The Oakland was one | 19 |
| The Oakland Oaks' league, for short | 39 |
| The Oak ___ Boys | 16 |
| The oak tree | 12 |
| The oak | 7 |
| The O.M. | 8 |
| The O.A.S. is one | 17 |
| The O's play in it | 22 |