| Answer | Crossword Clue |
|---|---|
| DEBS | Five-time candidate for U.S. Presidency |
| DEBS | Five-time U.S. presidential candidate in the early 1900s |
| NADER | Three-time U.S. presidential candidate |
| SAMPRAS | Five-time U.S. Open champ |
| GRAF | Five-time U.S. Open champ |
| GRAF | Five-time U.S. Open winner |
| SAMPRAS | Five-time U.S. Open winner |
| GRAF | Five-time U.S. Open champ Steffi |
| CONNORS | Five-time winner of the U.S. Open |
| TAIBABILONIA | Five-time U.S. Figure Skating Championships gold medalist |
| KELSO | Only five-time U.S. Horse of the Year |
| MIAHAMM | Five-time U.S. Soccer Athlete of the Year |
