| Two-time Triple Crown jockey | 28 |
| Two-time Triple Crown winner | 28 |
| Two-time U. S. Open winner Stewart | 34 |
| Two-time U.S. Open champ | 24 |
| Two-time U.S. Open champ Andre | 30 |
| Two-time U.S. Open champ Stewart | 32 |
| Two-time U.S. Open champion | 27 |
| Two-time U.S. Open champion Ernie | 33 |
| Two-time U.S. Open golf champion | 32 |
| Two-time U.S. Open tennis champ | 31 |
| Two-time U.S. Open winner | 25 |
| Two-time U.S. Open winner Andre | 31 |
| Two-time U.S. Open winner Ernie | 31 |
| Two-time U.S. Open winner Fraser | 32 |
| Two-time U.S. Open winner Hart | 30 |
| Two-time U.S. Open winner Monica | 32 |
| Two-time U.S. Open winner Retief | 32 |
| Two-time U.S. Open winner Stewart | 33 |
| Two-time U.S. Open winner Tony | 30 |
| Two-time U.S. Open winner Trevino | 33 |
| Two-time U.S. Women's Open winner | 37 |
| Two-time US Open champ | 22 |
| Two-time US Open Champion North | 31 |
| Two-time US Open winner | 23 |
| Two-time US Open winner Ernie | 29 |
| Two-time US Open winner Monica | 30 |
| Two-time US Women's Open golf champion Juli | 47 |
| Two-time Venezuelan president Carlos | 36 |
| Two-time victor over AES | 24 |
| Two-time Wimbledon champ | 24 |
| Two-time Wimbledon winner | 25 |
| Two-time Wimbledon winner Gibson | 32 |
| Two-time Wimbledon winner ___ Hoad | 34 |
| Two-time winner of the Hart Trophy | 34 |
| Two-time winner of the Masters | 30 |
| Two-time winner of the Women's World Cup | 44 |
| Two-time Winter Olympics city | 29 |
| Two-time Winter Olympics host | 29 |
| Two-time Women's Open champ | 31 |
| Two-time World Cup winners from S.A. | 36 |
| Two-time world figure skating champ Slutskaya | 45 |
| Two-time World Series champs | 28 |
| Two-time world skating champ Albright | 37 |
| Two-timed | 9 |
| Two-timer | 9 |
| Two-timer's liaison | 23 |
| Two-timer, e.g. | 15 |
| Two-timers | 10 |
| Two-times | 9 |
| Two-timing | 10 |
| Two-timing guy | 14 |
| Two-timing rodents? | 19 |
| Two-timing types | 16 |
| Two-tired transport | 19 |
| Two-to-one, e.g. | 16 |
| Two-to-one, for one | 19 |
| Two-to-one? | 11 |
| Two-toed bird | 13 |
| Two-toed creature | 17 |
| Two-toed sloth | 14 |
| Two-toed sloths | 15 |
| Two-ton beast | 13 |
| Two-ton predator | 16 |
| Two-tone | 8 |
| Two-tone coin | 13 |
| Two-tone cookie | 15 |
| Two-tone cookies | 16 |
| Two-tone dunker | 15 |
| Two-tone horse | 14 |
| Two-tone oxford | 15 |
| Two-tone oxfords | 16 |
| Two-tone sandwich cookie | 24 |
| Two-tone snack | 14 |
| Two-tone snacks | 15 |
| Two-tone treat | 14 |
| Two-tone treats | 15 |
| Two-tone whale | 14 |
| Two-toned cats | 14 |
| Two-toned coins | 15 |
| Two-toned cookie | 16 |
| Two-toned cookie treat | 22 |
| Two-toned cookies | 17 |
| Two-toned horses | 16 |
| Two-toned sea predator | 22 |
| Two-toned treat | 15 |
| Two-toned trotters | 18 |
| Two-toned Turkish coin | 22 |
| Two-topper line from Liza? | 26 |
| Two-track | 9 |
| Two-trailer rig | 15 |
| Two-two, for one | 16 |
| Two-under-par coups | 19 |
| Two-under-par feat | 18 |
| Two-under-par score | 19 |
| Two-under-pars | 14 |
| Two-unit home | 13 |
| Two-up, in Sydney | 17 |
| Two-walled fortification | 24 |
| Two-way | 7 |
| Two-way action | 14 |