| Five-time Art Ross Trophy winner, for short | 43 |
| Five-time Art Ross Trophy winner Phil, to fans | 46 |
| Five-time Art Ross Trophy winner | 32 |
| Five-time American Crossword Puzzle Tournament winner | 53 |
| Five-time also-ran | 18 |
| Five-time All-Star second baseman Chase ___ | 43 |
| Five-time All-Star second baseman | 33 |
| Five-time all-star catcher Santiago | 35 |
| Five-time All-Pro QB Luckman | 28 |
| Five-time A.L. batting champion | 31 |
| Five-time A.L. batting champ Boggs | 34 |
| Five-time A.L. batting champ | 28 |
| Five-time 30-game winner of early baseball | 42 |
| Five-time 1970s Phillies All-Star shortstop | 43 |
| Five-time 1970s Gold Glove winner César | 42 |
| Five-time "Sports Illustrated" swimsuit cover girl | 60 |
| Five-time "Hill Street Blues" Emmy nominee | 52 |
| Five-time "ER" Emmy nominee | 37 |
| Five-thirds of XCIII | 20 |
| Five-thirds of DCXXXVI | 22 |
| Five-term sen., say | 19 |
| Five-term Mexican president Benito | 34 |
| Five-term Mexican president | 27 |
| Five-stringed African lyre | 26 |
| Five-star W.W. II hero, informally | 34 |
| Five-star reviews | 17 |
| Five-star review | 16 |
| Five-star opposite? | 19 |
| Five-star off. | 14 |
| Five-star nickname | 18 |
| Five-star name | 14 |
| Five-star monogram | 18 |
| Five-star leader | 16 |
| Five-star initials | 18 |
| Five-star hotel offerings | 25 |
| Five-star hotel amenity | 23 |
| Five-star headline name of 1934 | 31 |
| Five-star general Bradley | 25 |
| Five-star gen. of WWII | 22 |
| Five-star first name | 20 |
| Five-star entree of angel-hair pasta? | 37 |
| Five-star Bradley | 17 |
| Five-star admiral | 17 |
| Five-star '50s initials | 27 |
| Five-star | 9 |
| Five-spots in card games | 24 |
| Five-spots | 10 |
| Five-spot | 9 |
| Five-spice powder ingredient | 28 |
| Five-speed unit | 15 |
| Five-speed options | 18 |
| Five-sou piece in Louis XIV's day | 37 |
| Five-sixths of a dozen | 22 |
| Five-sided pods | 15 |
| Five-sided plate | 16 |
| Five-sided home? | 16 |
| Five-sided corner of a diamond | 30 |
| Five-sided building in Va. | 26 |
| Five-sided base | 15 |
| Five-seeded fruit | 17 |
| Five-ring org. | 14 |
| Five-rayed seabed dweller | 25 |
| Five-rayed ocean creatures | 26 |
| Five-pointers in the sea | 24 |
| Five-pointer | 12 |
| Five-pointed star | 17 |
| Five-pointed ocean denizen | 26 |
| Five-pointed creature | 21 |
| Five-pillared faith | 19 |
| Five-petal flower | 17 |
| Five-peseta coin | 16 |
| Five-part HS exam | 17 |
| Five-paragraph response, perhaps | 32 |
| Five-paragraph piece, perhaps | 29 |
| Five-paragraph assignment, perhaps | 34 |
| Five-o'clock shadow | 23 |
| Five-O member | 13 |
| Five-O detective, to McGarrett | 30 |
| Five-O booking agent | 20 |
| Five-note refrain | 17 |
| Five-ninths of MLXXXIX | 22 |
| Five-night-a-week NBC star | 26 |
| Five-minute NHL periods | 23 |
| Five-min. periods, maybe | 24 |
| Five-min. NBA periods | 21 |
| Five-liners named for an Irish port | 35 |
| Five-liners named for an Irish county | 37 |
| Five-liners | 11 |
| Five-letter song refrain | 24 |
| Five-letter news channel | 24 |
| Five-legged calf, e.g. | 22 |
| Five-irons | 10 |
| Five-iron, once | 15 |
| Five-in-a-row wins | 18 |
| Five-in-a-row game that uses a go board | 39 |
| Five-in-a-row game | 18 |
| Five-in-a-row board game played with stones | 43 |
| Five-in-a-row board game created in 1978 | 40 |
| Five-hundredth anniversary | 26 |
| Five-generation political family | 32 |