| FLOYDMAYWEATHER | U.S. former boxer and world champion in five different weight classes, nicknamed Pretty Boy (5,10) |
| EVANDER | --- Holyfield, U.S. former boxer (7) |
| GRAZIANO | Rocky ___, American boxer and world middleweight champion. |
| MAYWEATHER | Floyd, U.S. boxing promoter and ex-boxer born in 1977, nicknamed Pretty Boy (10) |
| FLOYD | Which Depression-era gangster was nicknamed Pretty Boy? (5) |
| VINDICATES | Champions in five shows (10) |
| SUGAR | Nickname of former Olympic and world champion professional boxer Ray Leonard (5) |
| UREN | Which former boxer and POW on the Burma-Thailand railway became Minister for Urban and Regional Development in the Whitlam Labor government? (4) |
| LUKE | British darts player who is the current World No. 1 and World Champion, _ Humphries (4) |
| STEWART | Jackie --, Scottish racing driver and world champion who also excelled at clay-pigeon shooting |
| ADAMS | Nicola -----, former boxer and 2020 Strictly Come Dancing contestant (5) |
| JOE | Former boxer and reality TV star, _ Calzaghe (3) |
| SUGARRAYLEONARD | Boxing great who won world titles in five weight classes (5,3,7) |
| CONORMCGREGOR | UFC champion in two different weight classes and the highest-paid athlete of 2021: 2 wds. |
| PACQUIAO | Boxer with titles in eight different weight classes |
| PACQUAIO | Manny, Filipino former boxer who was world champion in eight different weight divisions (8) |
| WBO | Grp. recognizing international titleholders in different weight classes |
| IVAN | Identify the first name of this former legend who is the only man in professional tennis history to have a match winning percentage of over 90% in five different years. (4) |
| BENAINSLIE | The first person to win medals in five different Olympic Games in sailing |
| OSCARDELAHOYA | 1992 Olympic lightweight gold medalist who was a world champion boxer in six weight classes: 4 wds. |
