| Two-time Olympic skater | 23 |
| Two-time opponent for Ike | 25 |
| Two-time opponent of DDE | 24 |
| Two-time opponent of Ike | 24 |
| Two-time Oscar nominee Joan | 27 |
| Two-time Oscar nominee Mineo | 28 |
| Two-time Oscar nominee Shire | 28 |
| Two-time Oscar winner Dianne | 28 |
| Two-time Oscar winner Luise | 27 |
| Two-time Oscar winner Michael | 29 |
| Two-time Oscar winner Wiest | 27 |
| Two-time Oscar-winner Jackson | 29 |
| Two-time Oscars host Stewart | 28 |
| Two-time player of Elizabeth | 28 |
| Two-time president of Romania | 29 |
| Two-time president of Texas | 27 |
| Two-time Pulitzer composer | 26 |
| Two-time Quarry opponent | 24 |
| Two-time role for Angelina | 26 |
| Two-time role for Banderas | 26 |
| Two-time role for Hopkins | 25 |
| Two-time Smythe Trophy winner | 29 |
| Two-time South African PM | 25 |
| Two-time Super Bowl losers | 26 |
| Two-time Tony winner Alfred | 27 |
| Two-time Tony winner Finneran | 29 |
| Two-time Tony winner Judith | 27 |
| Two-time Tony winner Rivera | 27 |
| Two-time Triple Crown jockey | 28 |
| Two-time Triple Crown winner | 28 |
| Two-time U.S. Open champ | 24 |
| Two-time U.S. Open champion | 27 |
| Two-time U.S. Open winner | 25 |
| Two-time US Open champ | 22 |
| Two-time US Open winner | 23 |
| Two-time US Open winner Ernie | 29 |
| Two-time victor over AES | 24 |
| Two-time Wimbledon champ | 24 |
| Two-time Wimbledon winner | 25 |
| Two-time Winter Olympics city | 29 |
| Two-time Winter Olympics host | 29 |
| Two-time World Series champs | 28 |
| Two-timer's liaison | 23 |
| Two-tone sandwich cookie | 24 |
| Two-toned cookie treat | 22 |
| Two-toned sea predator | 22 |
| Two-toned Turkish coin | 22 |
| Two-topper line from Liza? | 26 |
| Two-walled fortification | 24 |
| Two-way communications device | 29 |
| Two-way poetic preposition | 26 |
| Two-way, as a sprinkler | 23 |
| Two-wheeled artillery wagons | 28 |
| Two-wheeled conveyance | 22 |
| Two-wheeled covered carriage | 28 |
| Two-wheeled transport? | 22 |
| Two-wheeler with gears | 22 |
| Two-wheelers in the rain? | 25 |
| Two-wheeling Armstrong | 22 |
| Two-word anagram for tale | 25 |
| Two-year-old male red deer | 26 |
| Two-year-old's assertion | 28 |
| Two-year-old's chorus | 25 |
| Two-year-old, at times | 22 |
| Two-year-old, unshorn sheep | 27 |
| Two-year-olds' chorus | 25 |
| Two-year-olds' utterances | 29 |
| Two-yr. humanities degrees | 26 |
| Two-__ (old short films) | 24 |
| Two-___ (ballroom dance) | 24 |
| Two-___ (court situation) | 25 |
| Two-___ (extended TV episode) | 29 |
| Two-___ (fox trot forerunner) | 29 |
| Two-___ (kind of fastball) | 26 |
| Two-___ (movie shorts) | 22 |
| Two-___ (some bathing suits) | 28 |
| Twosome in a downhill run | 25 |
| Twosome in a gossip column | 26 |
| Twosome in the gossip columns | 29 |
| Twosome you read about | 22 |
| Twosome, in a gossip column | 27 |
| Twosome, tabloid-style | 22 |
| Twosomes in the tabloids | 24 |
| Twosomes in the tabloids? | 25 |
| Twyla, the choreographer | 24 |
| Txted word of polite request | 28 |
| Ty Cobb's sobriquet | 23 |
| Ty with batting titles | 22 |
| Ty-D- -- (bathroom brand) | 25 |
| Tybalt's dispatcher | 23 |
| Tycho Brahe's sci. | 22 |
| Tycoon aboard the Christina | 27 |
| Tycoon Walton with a club | 25 |
| Tycoon's car, for short | 27 |
| Tyga "Switch ___" | 27 |
| Tying run, for instance | 23 |
| Tying-over line, in music | 25 |
| Tyke's dinnertime perch | 27 |
| Tyke's four-wheeler | 23 |
| Tykes TV show or movie | 22 |