| 100% | BRR | 3 | "I should have worn a scarf!" |
| 60% | BRRR | 4 | “I should have worn my winter coat!” |
| 56% | BRR | 3 | "I should've worn a jacket!" |
| 51% | DUH | 3 | "Oh, I should have known!" |
| 50% | DUH | 3 | "Oh, I should have known that!" |
| 50% | DUH | 3 | "Wow, I should have realized that!" |
| 49% | SINGOFOMISSION | 14 | Perform the hit "Things I Should Have Said"? |
| 48% | NECK | 4 | Where a scarf is worn |
| 47% | NOWONDER | 8 | "Ah, that explains it! I should have known": 2 wds. |
| 47% | BUNDLEUP | 8 | "Better wear a scarf and hat out there" (2 wds.) |
| 46% | DUH | 3 | "That should have been obvious to me" |
| 46% | BIKESHOP | 8 | Store that really should have a spokesperson |
| 46% | SOCKDRAWER | 10 | Place where everything should have a mate |
| 46% | LETSTALK | 8 | "We should have a conversation" (2 wds.) |
| 46% | ASCOT | 5 | Scarf worn like a tie |
| 46% | MYTHAIMAITAI | 12 | A Bangkok drink I had? |
| 45% | DUH | 3 | "Oh, that should have been obvious to me" |
| 45% | ENVY | 4 | "It should have happened to me instead" feeling |
| 45% | DUH | 3 | "Well, that certainly should have occurred to me!" |
| 45% | FIRSTAID | 8 | Everyone should have a kit like this one |
| 45% | EPA | 3 | Government org. that should have a clean record? |
| 45% | AGO | 3 | "We should have done this a long time ___" |
| 45% | LIAR | 4 | "A ___ should have a good memory": Quintilian |
| 45% | SWARAJ | 6 | "___ is my birthright and I shall have it" (rallying cry for Indian independence) |
| 45% | HAMMER | 6 | "If I Had a ___" |
| 45% | HAMMER | 6 | "If I had a ___ " |
| 45% | HAMMER | 6 | "If I Had a __" |
| 45% | MRT | 3 | Who said "When I'm ready to fight, my opponent has a better chance for surviving a forest fire wearing gasoline drawers" |
| 44% | BEER | 4 | It should have a head and a good body |
| 44% | BLADE | 5 | A fan should at least have one |