| Two-time Pulitzer-winning journalist | 36 |
| Two-time Pulitzer-winning playwright | 36 |
| Two-time Quarry opponent | 24 |
| Two-time role for Angelina | 26 |
| Two-time role for Banderas | 26 |
| Two-time role for Christina Ricci | 33 |
| Two-time role for Emma Thompson | 31 |
| Two-time role for Hopkins | 25 |
| Two-time role for Sidney Poitier | 32 |
| Two-time Romanian president Ion | 31 |
| Two-time runner-up at the Masters | 33 |
| Two-time running mate of Richard | 32 |
| Two-time screen role for Arnold Schwarzenegger | 46 |
| Two-time Senior PGA Championship winner Jay | 43 |
| Two-time Sixth Man of the Year Kevin | 36 |
| Two-time skating gold medalist Katarina | 39 |
| Two-time Smythe Trophy winner | 29 |
| Two-time South African PM | 25 |
| Two-time Stanley Cup winners in the 1970s | 41 |
| Two-time Super Bowl losers | 26 |
| Two-time Super Bowl M.V.P. Tom | 30 |
| Two-time Super Bowl MVP quarterback | 35 |
| Two-time tennis Grand Slam winner Rod | 37 |
| Two-time title role for Chris Hemsworth | 39 |
| Two-time Tony winner Alfred | 27 |
| Two-time Tony winner Bernadette | 31 |
| Two-time Tony winner did a no-no | 32 |
| Two-time Tony winner Finneran | 29 |
| Two-time Tony winner Judith | 27 |
| Two-time Tony winner Rivera | 27 |
| Two-time Tony-winning director McAnuff | 38 |
| Two-time Tony-winning playwright Yasmina __ | 43 |
| 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 |