| Text | Length |
| Most diminutive | 15 |
| Most diluted | 12 |
| Most dilettantish | 17 |
| Most dilapidated | 16 |
| Most dignified | 14 |
| Most diffident | 14 |
| Most difficult, as a problem | 28 |
| Most difficult to unravel | 25 |
| Most difficult to manage | 24 |
| Most difficult to find | 22 |
| Most difficult to fillet | 24 |
| Most difficult to climb | 23 |
| Most difficult to believe | 25 |
| Most difficult part | 19 |
| Most difficult moment, in a phrase | 34 |
| Most difficult foe | 18 |
| Most difficult | 14 |
| Most dice | 9 |
| Most diaphanous | 15 |
| Most dexterous | 14 |
| Most devious | 12 |
| Most detached | 13 |
| Most destitute | 14 |
| Most despicable | 15 |
| Most desperate | 14 |
| Most desolate | 13 |
| Most desired invitees | 21 |
| Most desired guests | 19 |
| Most desirable of goals | 23 |
| Most desirable invitees | 23 |
| Most desirable guests | 21 |
| Most desirable | 14 |
| Most desiccated | 15 |
| Most desert-like | 16 |
| Most derogatory, as a remark | 28 |
| Most derogatory | 15 |
| Most derisive, in a way | 23 |
| Most depressing | 15 |
| Most depressed | 14 |
| Most deplorable | 15 |
| Most dependable | 15 |
| Most denigrating | 16 |
| Most den mothers | 16 |
| Most demure | 11 |
| Most demanding | 14 |
| Most delightful | 15 |
| Most delicate | 13 |
| Most deliberate | 15 |
| Most delectable | 15 |
| Most delayed | 12 |
| Most definite | 13 |
| Most deeply felt | 16 |
| Most deep-piled | 15 |
| Most decent | 11 |
| Most debonair | 13 |
| Most dear | 9 |
| Most dauntless | 14 |
| Most darling | 12 |
| Most darkly droll | 17 |
| Most dark | 9 |
| Most daring | 11 |
| Most dapper | 11 |
| Most dangerous, as winter roads | 31 |
| Most damp | 9 |
| Most damning evidence, maybe | 28 |
| Most dainty | 11 |
| Most Cypriots, ethnically | 25 |
| Most cynical | 12 |
| Most cutting | 12 |
| Most curvaceous | 15 |
| Most curt | 9 |
| Most current news, with "the" | 39 |
| Most current | 12 |
| Most curmudgeonly | 17 |
| Most curious | 12 |
| Most cunning | 12 |
| Most cruel | 10 |
| Most crude | 10 |
| Most crowded | 12 |
| Most crosswords have one | 24 |
| Most cricket grounds | 20 |
| Most creepy | 11 |
| Most crazy | 10 |
| Most crafty | 11 |
| Most cozy | 9 |
| Most coveted position | 21 |
| Most coveted by collectors, perhaps | 35 |
| Most covered with oil | 21 |
| Most covered in grease | 22 |
| Most courteous | 14 |
| Most courageous | 15 |
| Most costly | 11 |
| Most corrupt | 12 |
| Most corrugated | 15 |
| Most corrosion-resistant metal | 30 |
| Most corpulent | 14 |
| Most cordial | 12 |
| Most coquettish | 15 |
| Most cool, to an old-school rapper | 34 |
| Most cool, in slang | 19 |
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