| Five-time Horse of the Year in the '60s | 43 |
| Five-time Horse of the Year, 1960-64 | 36 |
| Five-time Iditarod winner Rick | 30 |
| Five-time Japan Senior Open winner Aoki | 39 |
| Five-time Kentucky Derby winner | 31 |
| Five-time Kentucky Derby winner Bill | 36 |
| Five-time Kentucky Derby-winning jockey | 39 |
| Five-time Lady Byng Memorial Trophy winner | 42 |
| Five-time Masters champ | 23 |
| Five-time MLB All-Star Cooper | 29 |
| Five-time N.B.A. All-Star Chris | 31 |
| Five-time N.C.A.A. basketball champs from the A.C.C. | 52 |
| Five-time N.H.L. scoring leader of the 1990s-'00s | 53 |
| Five-time NBA championship-winning coach | 40 |
| Five-time NHL scoring leader Jaromir | 36 |
| Five-time NHL scoring leader Jaromir ___ | 40 |
| Five-time Olympic gold winner Nadia | 35 |
| Five-time Olympic gold-medal swimmer | 36 |
| Five-time Oscar nominee Adams | 29 |
| Five-time P.G.A. champ | 22 |
| Five-time PGA Championship winner | 33 |
| Five-time Presidential also-ran | 31 |
| Five-time Presidential candidate | 32 |
| Five-time Pro Bowl wide receiver Andre | 38 |
| Five-time Rose Bowl champs | 26 |
| Five-time Rose Bowl winner | 26 |
| Five-time Ryder Cup competitor | 30 |
| Five-time speed skating gold medalist | 37 |
| Five-time speed skating gold medalist Eric | 42 |
| Five-time Stanley Cup team | 26 |
| Five-time Sugar Bowl champs | 27 |
| Five-time Super Bowl champ | 26 |
| Five-time Super Bowl champions, informally | 42 |
| Five-time Super Bowl champs | 27 |
| Five-time Super Bowl champs, briefly | 36 |
| Five-time Super Bowl champs, for short | 38 |
| Five-time Super Bowl coach | 26 |
| Five-time Super Bowl winners | 28 |
| Five-time teammate of Bryant, Duncan, and Nowitzki at the NBA All-Star Game | 75 |
| Five-time Tour de France winner Indurain | 40 |
| Five-time Tour de France winner Miguel | 38 |
| Five-time U.S. Figure Skating Championships gold medalist | 57 |
| Five-time U.S. Open champ | 25 |
| Five-time U.S. Open champ Steffi | 32 |
| Five-time U.S. Open winner | 26 |
| Five-time U.S. presidential candidate in the early 1900s | 56 |
| Five-time Wimbledon champ | 25 |
| Five-time Wimbledon champ with iconic hair | 42 |
| Five-time Wimbledon champ, 1976-80 | 34 |
| Five-time Wimbledon champion | 28 |
| Five-time Wimbledon title holder | 32 |
| Five-time Wimbledon winner | 26 |
| Five-time winner of the Copa do Mundo | 37 |
| Five-time winner of the Rose Bowl | 33 |
| Five-time winner of the Tour de France | 38 |
| Five-time winner of the U.S. Open | 33 |
| Five-time world champion figure skater Carol | 44 |
| Five-time world figure skating champion Carol | 45 |
| Five-times-a-day Islamic prayer | 31 |
| Five-to-one, e.g. | 17 |
| Five-to-six-foot Aussie | 23 |
| Five-to-two, e.g. | 17 |
| Five-Wimbledon winner | 21 |
| Five-word greeting to an unknown addressee: abbr. | 49 |
| Five-year period | 16 |
| Five-year periods | 17 |
| Five-Year Plan empire | 21 |
| Five-Year Plan implementer, for short | 37 |
| Five-Year Plan nation | 21 |
| Five-year-old's recitation | 30 |
| Five: Comb. form | 16 |
| Five: Prefix | 12 |
| Fivefold | 8 |
| Fiver | 5 |
| Fiver face | 10 |
| Fiver units | 11 |
| Fivers | 6 |
| Fives | 5 |
| Fives and nines, e.g. | 21 |
| Fives and tens, e.g. | 20 |
| Fives and ___ | 13 |
| Fives, nines or elevens | 23 |
| Fivescore yrs. | 14 |
| Fivesome | 8 |
| Fivesome found in the five Tony winners in this puzzle | 54 |
| Fivesome on a five | 18 |
| Fivesome seen in order in the answer to each starred clue | 57 |
| Fivesomes | 9 |
| FiveThirtyEight datum | 21 |
| FiveThirtyEight owner | 21 |
| Fix | 3 |
| Fix as a broken window | 23 |
| Fix (a game) | 12 |
| Fix (in) | 8 |
| Fix (up) | 8 |
| Fix ... or damage | 17 |
| Fix a bandage | 13 |
| Fix a bartending mistake | 24 |
| Fix a basic math error | 22 |
| Fix a blockage | 14 |