| Five-time "Sports Illustrated" swimsuit cover girl | 60 |
| Five-time 1970s Gold Glove winner César | 42 |
| Five-time 1970s Phillies All-Star shortstop | 43 |
| Five-time 30-game winner of early baseball | 42 |
| Five-time A.L. batting champ | 28 |
| Five-time A.L. batting champ Boggs | 34 |
| Five-time A.L. batting champion | 31 |
| Five-time All-Pro QB Luckman | 28 |
| Five-time all-star catcher Santiago | 35 |
| Five-time All-Star second baseman | 33 |
| Five-time All-Star second baseman Chase ___ | 43 |
| Five-time also-ran | 18 |
| Five-time American Crossword Puzzle Tournament winner | 53 |
| Five-time Art Ross Trophy winner | 32 |
| Five-time Art Ross Trophy winner Phil, to fans | 46 |
| Five-time Art Ross Trophy winner, for short | 43 |
| Five-time aspirant for Presidency | 33 |
| Five-time baseball All-Star ___ Wills | 37 |
| Five-time Best Actress nominee Jessica | 38 |
| Five-time British Open champ | 28 |
| Five-time candidate for President | 33 |
| Five-time candidate for U.S. Presidency | 39 |
| Five-time Derby winner | 22 |
| Five-time Derby winner Eddie | 28 |
| Five-time Emmy award-winning actor | 34 |
| Five-time Emmy nominee Georgia | 30 |
| Five-time Emmy winner | 21 |
| Five-time Emmy winner Peter | 27 |
| Five-time Emmy winner Tina | 26 |
| Five-time Emmy-winning actress | 30 |
| Five-time Emmy-winning role | 27 |
| Five-time Fiesta Bowl champs, for short | 39 |
| Five-time Fiesta Bowl champs: Abbr. | 35 |
| Five-time French Open winner Rafael | 35 |
| Five-time gold winner Eric | 26 |
| Five-time Golden Glove winner César | 38 |
| Five-time Grammy winner for Best Rap Album | 42 |
| Five-time Grammy winner James | 29 |
| Five-time Horse of the Year | 27 |
| 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 |