| Two-time candidate Perot | 24 |
| Two-time British P.M. | 21 |
| Two-time Bond portrayer | 23 |
| Two-time Best Spoken Word Album Grammy winner | 45 |
| Two-time Best Situation Comedy Emmy winner | 42 |
| Two-time Best Rock Album Grammy winner | 38 |
| Two-time Best Director Oscar winner Lee | 39 |
| Two-time Best Adapted Screenplay Oscar winner | 45 |
| Two-time Best Actress winner Rainer | 35 |
| Two-time Best Actress winner | 28 |
| Two-time Best Actress Oscar winner Jackson | 42 |
| Two-time Best Actress Jackson | 29 |
| Two-time belligerent against the British Empire | 47 |
| Two-time batting champ Lefty | 28 |
| Two-time baseball All-Star Sandoval | 35 |
| Two-time Banderas role | 22 |
| Two-time Australian Open champ Williams | 39 |
| Two-time Art Ross Trophy winner | 31 |
| Two-time Argentine president | 28 |
| Two-time All-Star power forward Carlos | 38 |
| Two-time All-Star Polanco | 25 |
| Two-time All-Star Martinez | 26 |
| Two-time All-Pro cornerback currently with the Denver Broncos | 61 |
| Two-time achievement for the Chicago Bulls | 42 |
| Two-time ABA champs | 19 |
| Two-time A.L. M.V.P. | 20 |
| Two-time A.L. homer leader Thomas | 33 |
| Two-time A.L. home run champ Tony | 33 |
| Two-time 1990s A.L. batting champ Edgar | 39 |
| Two-time 1980s skating gold medalist Katarina | 45 |
| Two-time 1980s skating gold medalist | 36 |
| Two-time 1970s NBA champs | 25 |
| Two-time 1500-meter Olympic gold medalist | 41 |
| Two-time "Rolling Stone" cover subject in 1981 | 56 |
| Two-time "MASH" Emmy winner | 37 |
| Two-time "Dancing with the Stars" winner Julianne | 59 |
| Two-time "Dancing With the Stars" co-winner Julianne | 62 |
| Two-time '90s US Open champ | 31 |
| Two-time '80s-'90s Senate majority leader | 49 |
| Two-time '70s Stanley Cup champs | 36 |
| Two-time | 8 |
| Two-tiered galley | 17 |
| Two-thumbs-up review | 20 |
| Two-thumbs-down reviews | 23 |
| Two-thirds off? | 15 |
| Two-thirds of the Belmont Stakes | 32 |
| Two-thirds of sesqui- | 21 |
| Two-thirds of Santa's laugh | 31 |
| Two-thirds of r.b.i. | 20 |
| Two-thirds of H.M.S. | 20 |
| Two-thirds of Earth | 19 |
| Two-thirds of dodeca- | 21 |
| Two-thirds of DIY | 17 |
| Two-thirds of D.I.Y. | 20 |
| Two-thirds of D.D.E. | 20 |
| Two-thirds of AOL | 17 |
| Two-thirds of a Three Tenors selection | 38 |
| Two-thirds of a magnum | 22 |
| Two-thirds of a dozen | 21 |
| Two-thirds of a double-play combo | 33 |
| Two-thirds of a canine star | 27 |
| Two-thirds of 10% of DCCXCV | 27 |
| Two-terminal semiconductor | 26 |
| Two-terminal device | 19 |
| Two-term prez | 13 |
| Two-term presidents' terms, e.g. | 36 |
| Two-term presidents' tenures, e.g. | 38 |
| Two-term governor and three-term senator from Nebraska | 54 |
| Two-team wrestling meets | 24 |
| Two-tailed flag | 15 |
| Two-tab dinners for two | 23 |
| Two-syllable unit | 17 |
| Two-syllable shout | 18 |
| Two-syllable poetic unit | 24 |
| Two-syllable poetic foot | 24 |
| Two-syllable foot, in poetry | 28 |
| Two-syllable foot | 17 |
| Two-syllable feet | 17 |
| Two-sword | 9 |
| Two-stroke drumbeats | 20 |
| Two-stroke drumbeat | 19 |
| Two-stripers, e.g.: Abbr. | 25 |
| Two-stripers (abbr.) | 20 |
| Two-striper in the Army: Abbr. | 30 |
| Two-striper (abbr.) | 19 |
| Two-striper | 11 |
| Two-stripe soldier: Abbr. | 25 |
| Two-story apartment | 19 |
| Two-step direction, perhaps | 27 |
| Two-star system | 15 |
| Two-star performance? | 21 |
| Two-star flag officer | 21 |
| Two-star | 8 |
| Two-stage missile | 17 |
| Two-spot and six-spot? | 22 |
| Two-spot | 8 |
| Two-sport Sanders | 17 |
| Two-speaker system | 18 |
| Two-somes | 9 |
| Two-sidedness | 13 |