| Olds classics | 13 |
| Olds classic | 12 |
| Olds cars | 9 |
| Olds car | 8 |
| Olds antiques | 13 |
| Olds 442 rivals | 15 |
| Oldman's "JFK" role | 33 |
| Oldman or Sinise | 16 |
| Oldman or Newman | 16 |
| Oldish youngster | 16 |
| Oldish means of connecting | 26 |
| Oldies-lover's request? | 27 |
| Oldies syllable | 15 |
| Oldies refrain syllable | 23 |
| Oldies players | 14 |
| Oldies player | 13 |
| Oldies group, ___ Na Na | 23 |
| Oldies group ___ Na Na | 22 |
| Oldies group -- Na Na | 21 |
| Oldies evocation | 16 |
| Oldie with a star character named Stone | 39 |
| Oldie with "all alone and feeling blue" | 49 |
| Oldie syllable | 14 |
| Oldie recorded by Midler in '72 | 35 |
| Oldie introduced by Ethel Waters: 1924 | 38 |
| Oldie by the Dell-Vikings | 25 |
| Oldfangled | 10 |
| Oldest, as jokes | 16 |
| Oldest winner of the Indianapolis 500 at 47 | 43 |
| Oldest von Trapp child in "The Sound of Music" | 56 |
| Oldest US tech university | 25 |
| Oldest U.S. settlement west of the Rockies | 42 |
| Oldest U.S. hoops contest | 25 |
| Oldest U.S. department store chain | 34 |
| Oldest U.S. civil liberties org. | 32 |
| Oldest U.S. capital | 19 |
| Oldest technological univ. in America | 37 |
| Oldest synagogue in the U.S., in Newport, R.I. | 46 |
| Oldest street in L.A. | 21 |
| Oldest state capital | 20 |
| Oldest son of Shem | 18 |
| Oldest Smurf | 12 |
| Oldest signer of the Declaration of Independence | 48 |
| Oldest settler in the West? | 27 |
| Oldest settler in the west | 26 |
| Oldest republic in Africa | 25 |
| Oldest printed song for Yuletide | 32 |
| Oldest president | 16 |
| Oldest permanent settlement in Ohio | 35 |
| Oldest of the Stooges | 21 |
| Oldest of the Rice Krispies brothers | 36 |
| Oldest of the Marxes | 20 |
| Oldest of the Hawaiian Islands | 30 |
| Oldest of the gods, in Plato's "Symposium" | 56 |
| Oldest of the Fab Four | 22 |
| Oldest of the Bridges | 21 |
| Oldest of the Brady kids | 24 |
| Oldest of the Brady bunch | 25 |
| Oldest of the Beatles | 21 |
| Oldest of the Baldwin brothers | 30 |
| Oldest of the Baldwin boys | 26 |
| Oldest of the "Little Women" | 38 |
| Oldest of the "Animaniacs" siblings | 45 |
| Oldest of a trio of comedic brothers | 36 |
| Oldest of a literary trio | 25 |
| Oldest of a literary quartet | 28 |
| Oldest of a group | 17 |
| Oldest New England town | 23 |
| Oldest national park | 20 |
| Oldest musketeer | 16 |
| Oldest military fliers | 22 |
| Oldest member of Hanson | 23 |
| Oldest March girl | 17 |
| Oldest man in space John | 24 |
| Oldest major league ballpark | 28 |
| Oldest living thing in Middle Earth | 35 |
| Oldest living First Lady | 24 |
| Oldest Little Leaguers | 22 |
| Oldest known oil source | 23 |
| Oldest known form of currency | 29 |
| Oldest known city in Belgium | 28 |
| Oldest kid on "Family Guy" | 36 |
| Oldest Indy winner | 18 |
| Oldest Indy 500 winner | 22 |
| Oldest independent country in Europe | 36 |
| Oldest in a delivery line? | 26 |
| Oldest Greek in the Trojan War | 30 |
| Oldest golfer to win the U.S. Open | 34 |
| Oldest Gabor sister | 19 |
| Oldest feminine org. in the U.S. | 32 |
| Oldest driver to win the Indy 500 | 33 |
| Oldest driver to win the Indianapolis 500 | 41 |
| Oldest desert in the world | 26 |
| Oldest daughter on "Jon & Kate Plus 8" | 52 |
| Oldest continuous democracy in Central America | 46 |
| Oldest city in Ohio | 19 |
| Oldest city in Greece | 21 |
| Oldest city in Colombia | 23 |
| Oldest child in the comic strip "Baby Blues" | 54 |
| Oldest child | 12 |