| 100% | ORATOR | 6 | Winston Churchill, notably |
| 64% | TORY | 4 | Winston Churchill, politically |
| 64% | VSIGN | 5 | Winston Churchill gesture |
| 64% | SIR | 3 | ___ Winston Churchill |
| 63% | AFAR | 4 | Winston Churchill's "___ Country" |
| 63% | TORY | 4 | Winston Churchill, e.g. |
| 63% | VSIGN | 5 | Winston Churchill flashed it |
| 63% | SIR | 3 | Winston Churchill's title |
| 63% | RANDOLPH | 8 | Winston Churchill's son |
| 63% | NEVER | 5 | Winston Churchill; ___, ___, ___ give up! |
| 62% | JEROME | 6 | Winston Churchill's mother, Jennie __ |
| 60% | POODLE | 6 | Winston Churchill's Rufus, for one |
| 60% | CANE | 4 | Prop for Winston Churchill |
| 60% | SIR | 3 | Title for Winston Churchill |
| 57% | BEZIQUE | 7 | Favorite card game of Winston Churchill |
| 57% | BLENHEIMPALACE | 14 | Sir Winston Churchill's ancestral home |
| 56% | ONEWHOCANT | 10 | Winston Churchill's description of a fanatic, part 1 |
| 56% | PRISONEROFWAR | 13 | Jean-Paul Sartre or Winston Churchill, once |
| 56% | SIRENSUIT | 9 | One-piece overalls, linked with Winston Churchill |
| 56% | BOWTIES | 7 | Donald Duck and Winston Churchill wear them |
| 54% | HOUR | 4 | "Darkest ___" (2017 Winston Churchill biopic starring Gary Oldman) |
| 54% | FINESTHOUR | 10 | Time of valor, in a Winston Churchill speech |
| 54% | CIGAR | 5 | Trademark item for Groucho Marx or Winston Churchill |
| 54% | JOWLS | 5 | Droopy facial features on Winston Churchill and bulldogs |
| 53% | HELL | 4 | "If you're going through ___, keep going": Winston Churchill |
| 53% | OLDMAN | 6 | Actor Gary who plays Winston Churchill in "Darkest Hour" |
| 53% | THECROWN | 8 | Netflix show on which John Lithgow plays Winston Churchill |
| 51% | BOERWAR | 7 | Subject of Winston Churchill's "London to Ladysmith via Pretoria" |
| 50% | TIMOTHY | 7 | ___ Spall, actor who played Winston Churchill in "The King's Speech" |
| 49% | ART | 3 | "Without tradition, ___ is a flock of sheep without a shepherd": Winston Churchill |