| 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| Like an outdated license | 24 |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 |
| Like an underdone steak | 23 |
| Like an undisciplined receiver coach? | 37 |
| Like an undistinguished hotel | 29 |
| Like an uneventful day at the ladder company? | 45 |
| Like an unexciting tournament? | 30 |
| Like an unexpectedly large gift | 31 |
| Like an unfiltered cigarette, maybe | 35 |
| Like an unflipped fried egg | 27 |
| Like an unfortunate torero | 26 |
| Like an unfriendly stare | 24 |
| Like an unhelpful explanation | 29 |
| Like an uninhabited preserve | 28 |
| Like an unkempt lawn | 20 |
| Like an unlucky encierro participant | 36 |
| Like an unlucky thief | 21 |
| Like an unlucky winter pedestrian | 33 |
| Like an unmade bed | 18 |
| Like an unmatched sock | 22 |
| Like an unopened Zinfandel | 26 |
| Like an unpaid policy | 21 |
| Like an unreal land? | 20 |
| Like an unrinsed washer load | 28 |
| Like an unspoiled paradise | 26 |
| Like an unstoppable athlete, figuratively | 41 |
| Like an unswept fireplace | 25 |
| Like an unswept hearth | 22 |
| Like an untended garden | 23 |
| Like an untended lawn | 21 |
| Like an unusual occurrence | 26 |
| Like an unwatched pot | 21 |
| Like an unweeded garden | 23 |
| Like an unwelcome diplomat | 26 |
| Like an unwritten exam | 22 |
| Like an uphill battle? | 22 |
| Like an upraised eyebrow | 24 |
| Like an x or y line | 19 |
| Like an X-rated film | 20 |
| Like Ananias | 12 |
| Like anarchy | 12 |
| Like anatomical anvils | 22 |
| Like anchors | 12 |
| Like anchovies | 14 |
| Like anchovies, often | 21 |
| Like anchovy pizza, stereotypically | 35 |
| Like ancient canyon cliffs | 26 |
| Like Andean pyramids | 20 |
| Like Andersen's duckling | 28 |
| Like Anderson Cooper, finally | 29 |
| Like andirons, generally | 24 |
| Like Andy Capp after a pub crawl | 32 |
| Like Andy Rooney | 16 |
| Like angel cakes | 16 |
| Like angel food cake | 20 |
| Like angel-food cake | 20 |
| Like Angela in "Angela's Ashes" | 45 |
| Like angels | 11 |
| Like angels we have heard? | 26 |
| Like angles between 90 and 180 degrees | 38 |
| Like angles less than 90 degrees | 32 |
| Like Angora cats | 16 |