| Like an oeil-de-boeuf window | 28 |
| Like an off-key football lineman? | 33 |
| Like an off-pitch piano | 23 |
| Like an offer that's under actual value | 43 |
| Like an officious intermeddler | 30 |
| Like an oily mitt | 17 |
| Like an old Andean empire | 25 |
| Like an old apartment | 21 |
| Like an old apple, maybe | 24 |
| Like an old auto | 16 |
| Like an old bagel | 17 |
| Like an old bialy | 17 |
| Like an old bucket of song | 26 |
| Like an old chestnut | 20 |
| Like an old cigar | 17 |
| Like an old cliche | 18 |
| Like an old cuss | 16 |
| Like an old English coin worth 21 shillings | 43 |
| Like an old Frankfurter | 23 |
| Like an old grate | 17 |
| Like an old hand | 16 |
| Like an old joke | 16 |
| Like an old lady (anagram of ELIAN) | 35 |
| Like an old loaf | 16 |
| Like an old look looking good again | 35 |
| Like an old man? | 16 |
| Like an old mattress | 20 |
| Like an old Norse poem | 22 |
| Like an old oak tree | 20 |
| Like an old pay telephone call | 30 |
| Like an old piano | 17 |
| Like an old print job | 21 |
| Like an old record | 18 |
| Like an old saw | 15 |
| Like an old schoolhouse | 23 |
| Like an old sofa | 16 |
| Like an old sweater | 19 |
| Like an old tree trunk | 22 |
| Like an old TV: Abbr. | 21 |
| Like an old woman | 17 |
| Like an old wristwatch, in more ways that one | 45 |
| Like an old wristwatch? | 23 |
| Like an omelet | 14 |
| Like an omelet, e.g. | 20 |
| Like an onion in a Gibson | 25 |
| Like an open bottle of champagne | 32 |
| Like an open pasture | 20 |
| Like an open secret | 19 |
| Like an opera song | 18 |
| Like an opossum's tail | 26 |
| Like an optimist's glass | 28 |
| Like an optimist's glasses? | 31 |
| Like an optimist's outlook | 30 |
| Like an optimist's point of view | 36 |
| Like an oracle | 14 |
| Like an oral exam | 17 |
| Like an oral exam, often | 24 |
| Like an Oreo cookie, colorwise | 30 |
| Like an oriel | 13 |
| Like an Oscars gala | 19 |
| Like an otary | 13 |
| Like an otological test | 23 |
| Like an otter's feet | 24 |
| Like an out-of-state elector's ballot | 41 |
| Like an out-of-style garment that's in style | 48 |
| Like an outdated license | 24 |
| Like an outdoor painting | 24 |
| Like an outdoorsy Englishman | 28 |
| Like an outstanding mail carrier? | 33 |
| Like an overcast night | 22 |
| Like an overcast sky | 20 |
| Like an overdue letter to a friend | 34 |
| Like an overlook view | 21 |
| Like an overripe melon | 22 |
| Like an oversized magazine? | 27 |
| Like an overventilated room | 27 |
| Like an owl | 11 |
| Like an owl's eyes | 22 |
| Like an owl, proverbially | 25 |
| Like an ox | 10 |
| Like an oxeye window | 20 |
| Like an Oz man | 14 |
| Like an Oz resident's makeup | 32 |
| Like an rodent-infested warehouse | 33 |
| Like an S.R.O. theater | 22 |
| Like an SASE, often | 19 |
| Like an SST | 11 |
| Like an unassisted triple play | 30 |
| Like an unbelievable story | 26 |
| Like an unborn baby's position | 34 |
| Like an uncaught escapee | 24 |
| Like an unchallenged receiver | 29 |
| Like an uncleaned fireplace | 27 |
| Like an uncleaned hearth | 24 |
| Like an uncomfortable landlubber | 32 |
| Like an uncomfortable mattress | 30 |
| Like an undeliverable pkg. | 26 |
| Like an undercooked egg | 23 |
| Like an undercover cop whose cover is blown | 43 |
| Like an underdeveloped country | 30 |