| Two-time Oscar-winning screenwriter | 35 |
| Two-time Oscar-winning director Lee | 35 |
| Two-time Oscar-winning director Frank ___ | 41 |
| Two-time Oscar-winning cinematographer Nykvist | 46 |
| Two-time Oscar-winner Jackson | 29 |
| Two-time Oscar winner Wiest | 27 |
| Two-time Oscar winner whose identity is "mistaken" in five puzzle answers | 83 |
| Two-time Oscar winner Michael | 29 |
| Two-time Oscar winner Luise | 27 |
| Two-time Oscar winner in the tub? | 33 |
| Two-time Oscar winner for Best Adapted Screenplay | 49 |
| Two-time Oscar winner Dianne | 28 |
| Two-time Oscar winner | 21 |
| Two-time Oscar nominee Shire | 28 |
| Two-time Oscar nominee Mineo | 28 |
| Two-time Oscar nominee Joan | 27 |
| Two-time Oscar nominee J. Carrol ___ | 36 |
| Two-time Oscar nominee for portraying Henry II | 46 |
| Two-time Oscar nominee as Henry II | 34 |
| Two-time opponent of Ike | 24 |
| Two-time opponent of DDE | 24 |
| Two-time opponent for Ike | 25 |
| Two-time Olympics gold-metal skater | 35 |
| Two-time Olympic slalom medalist Phil | 37 |
| Two-time Olympic skating medalist Michelle | 42 |
| Two-time Olympic skater | 23 |
| Two-time Olympic running gold medalist ___ Gebrselassie | 55 |
| Two-time Olympic pairs skating champ Ekaterina | 46 |
| Two-time Olympic ice-skating medalist Brian | 43 |
| Two-time Olivier Award winner Jacobi | 36 |
| Two-time NOW president Eleanor | 30 |
| Two-time Nobelist Pauling | 25 |
| Two-time Nobelist Marie | 23 |
| Two-time Nobelist | 17 |
| Two-time Nobel winner Marie | 27 |
| Two-time Nicaraguan president Chamorro | 38 |
| Two-time NFL MVP | 16 |
| Two-time Newbery winner ___ Lowry | 33 |
| Two-time Newbery winner Lowry | 29 |
| Two-time NBA MVP Steve | 22 |
| Two-time NBA MVP Karl | 21 |
| Two-time NBA all-star Vandeweghe | 32 |
| Two-time NBA All-Star Game MVP | 30 |
| Two-time national ticket candidate | 34 |
| Two-time National League MVP Murphy | 35 |
| Two-time National League MVP | 28 |
| Two-time National League batting champ Lefty | 44 |
| Two-time NASCAR champion Jarrett | 32 |
| Two-time NAACP Image award-winning actor | 40 |
| Two-time N.L. M.V.P., 1954 and 1965 | 35 |
| Two-time N.L. batting champ Richie | 34 |
| Two-time N.L. batting champ Lefty | 33 |
| Two-time N.B.A. M.V.P. Steve | 28 |
| Two-time N.B.A. All-Star Robinson | 33 |
| Two-time N.B.A. All-Star Brand | 30 |
| Two-time MVP quarterback | 24 |
| Two-time movie role for Dana | 28 |
| Two-time movie | 14 |
| Two-time Mexican president | 26 |
| Two-time Masters winner Bernhard | 32 |
| Two-time Masters champ | 22 |
| Two-time losing Republican presidential candidate | 49 |
| Two-time loser to McKinley | 26 |
| Two-time loser to Ike | 21 |
| Two-time loser to Graf at the US Open | 37 |
| Two-time loser to Dwight | 24 |
| Two-time loser to DDE | 21 |
| Two-time loser to D.D.E. | 24 |
| Two-time link | 13 |
| Two-time L.P.G.A. Championship winner Laura | 43 |
| Two-time L.P.G.A. champ born in Korea | 37 |
| Two-time Jack Nicklaus Trophy winner Jay | 40 |
| Two-time Italian prime minister Moro | 36 |
| Two-time Italian prime minister Giuliano | 40 |
| Two-time Italian prime minister Aldo | 36 |
| Two-time Italian prime minister | 31 |
| Two-time Israeli prime minister | 31 |
| Two-time Indy winner Luyendyk | 29 |
| Two-time Indy champ Luyendyk | 28 |
| Two-time Indy 500 winner ___ Luyendyk | 37 |
| Two-time Indy 500 winner Luyendyk | 33 |
| Two-time Indy 500 champ Luyendyk | 32 |
| Two-time Indian Prime Minister Gandhi | 37 |
| Two-time Hugo Award winner Gaiman | 33 |
| Two-time host of the Summer Olympics | 36 |
| Two-time host of the Olympics | 29 |
| Two-time heavyweight champ Patterson | 36 |
| Two-time Hart Trophy winner, familiarly | 39 |
| Two-time Haitian president Préval | 36 |
| Two-time Green Party candidate | 30 |
| Two-time green jacket wearer Bernhard | 37 |
| Two-time Greek P.M. Papandreou | 30 |
| Two-time Grand Slam winner | 26 |
| Two-time Grammy-winning pianist Peter | 37 |
| Two-time Grammy winner __ Lee Jones | 35 |
| Two-time Grammy winner Patti | 28 |
| Two-time Grammy winner Kathy | 28 |
| Two-time Grammy winner Jon | 26 |
| Two-time Grammy winner Houston | 30 |
| Two-time Grammy winner for Best Male Jazz Vocal Performance | 59 |