| 100% | IMEAN | 5 | "That should have been ..." |
| 100% | DUH | 3 | "Oh, that should have been obvious to me" |
| 99% | DIRTYOLDMENUS | 13 | Diner handouts that should have been replaced years ago? |
| 89% | WEWEREROBBED | 12 | "That should have been our victory!" |
| 88% | DUH | 3 | "That should have been obvious to me" |
| 82% | GOOGOL | 6 | The search engine name that should have been spelled this way, maybe because they had no search engine to check at the time? |
| 72% | IMEAN | 5 | Preceder of what should have been said |
| 71% | WRONG | 5 | Like "F," when it should have been "T" |
| 71% | EPA | 3 | Government org. that should have a clean record? |
| 70% | EMAIL | 5 | What many a pointless meeting really should have been |
| 69% | DUH | 3 | "I should have known that!" |
| 69% | SEEN | 4 | "I should have ___ that coming" |
| 69% | DUH | 3 | ''I should have known that!'' |
| 69% | BETTERIDEA | 10 | Alternative that should be followed |
| 69% | VICE | 4 | Habit that should be kicked |
| 69% | TYRANNY | 7 | Rule that should be broken? |
| 69% | EMAIL | 5 | What a pointless meeting probably should have been handled by |
| 68% | DUH | 3 | "Oh, I should have known that!" |
| 68% | DUH | 3 | "Wow, I should have realized that!" |
| 68% | DUH | 3 | "I should have known that!" expression |
| 68% | SORE | 4 | ___ subject (topic that should be avoided) |
| 68% | BALD | 4 | Like tires that should be retired |
| 68% | EVENIF | 6 | Should it be that |
| 67% | NOAH | 4 | He should have swatted those two flies |
| 67% | CUR | 3 | Dog that should be on a leash |
| 67% | AFTERTASTE | 10 | Finish that should be long and complex |
| 67% | IMPORTANT | 9 | Type of detail that should be noticed |
| 66% | IFSO | 4 | Should that be the case |
| 66% | SNUB | 4 | Someone who wasn't named a Pro Bowler, but should have been |
| 66% | TMI | 3 | "You should have kept that to yourself!": Abbr. |