| Oldest in a delivery line? | 26 |
| Oldest Indy 500 winner | 22 |
| Oldest known city in Belgium | 28 |
| Oldest known form of currency | 29 |
| Oldest known oil source | 23 |
| Oldest Little Leaguers | 22 |
| Oldest living First Lady | 24 |
| Oldest major league ballpark | 28 |
| Oldest man in space John | 24 |
| Oldest member of Hanson | 23 |
| Oldest military fliers | 22 |
| Oldest New England town | 23 |
| Oldest of a literary quartet | 28 |
| Oldest of a literary trio | 25 |
| Oldest of the Baldwin boys | 26 |
| Oldest of the Brady bunch | 25 |
| Oldest of the Brady kids | 24 |
| Oldest of the Fab Four | 22 |
| Oldest republic in Africa | 25 |
| Oldest settler in the west | 26 |
| Oldest settler in the West? | 27 |
| Oldest U.S. hoops contest | 25 |
| Oldest US tech university | 25 |
| Oldie by the Dell-Vikings | 25 |
| Oldies group ___ Na Na | 22 |
| Oldies group, ___ Na Na | 23 |
| Oldies refrain syllable | 23 |
| Oldies-lover's request? | 27 |
| Oldish means of connecting | 26 |
| Olds discontinued in 2004 | 25 |
| Olds introduced in '98 | 26 |
| Olds model for six years | 24 |
| Olds's last compact | 23 |
| Oldsmobile Cutlass model | 24 |
| Oldsmobile Cutlass ___ | 22 |
| Oldsmobile debut of 1998 | 24 |
| Oldsmobile model of 1999-2004 | 29 |
| Oldsmobile model, once | 22 |
| Oldsmobile of 1999-2004 | 23 |
| Oldsmobile's final model | 28 |
| Oldsmobile's last model | 27 |
| Oldster's nest egg | 22 |
| Oldster's nickname | 22 |
| Oldtime actress Massey | 22 |
| Oldtime crooner Julius | 22 |
| Oldtime gangster Bugsy | 22 |
| Ole Miss, athletically | 22 |
| Oleander "Why ___" | 28 |
| Olecranons are part of them | 27 |
| Oleg Cassini's concern | 26 |
| Oleoresin used as incense | 25 |
| Oleoresin used in incense | 25 |
| Olfactophobe's fear | 23 |
| Olfactory challenge, at times | 29 |
| Olfactory lobe's purpose | 28 |
| Olfactory nerve stimulator | 26 |
| Oligarch's relative | 23 |
| Oligophrenic's problem | 26 |
| Olin of "Alias" | 25 |
| Olin of "Chocolat" | 28 |
| Olin of "Havana" | 26 |
| Olios for actress Cartwright? | 29 |
| Olive -- (Popeye's gal) | 27 |
| Olive and corn, for two | 23 |
| Olive and linseed products | 26 |
| Olive and palm, for two | 23 |
| Olive first spotted in 1919 | 27 |
| Olive Garden selection | 22 |
| Olive Garden specialty | 22 |
| Olive in some cartoons | 22 |
| Olive in the funny pages | 24 |
| Olive in the funny papers | 25 |
| Olive of 'Popeye' | 25 |
| Olive of old funny pages | 24 |
| Olive of Thimble Theatre | 24 |
| Olive or corn follower | 22 |
| Olive or crude follower | 23 |
| Olive or her brother Castor | 27 |
| Olive or peanut extract | 23 |
| Olive or peanut product | 23 |
| Olive or sunflower extract | 26 |
| Olive Oyl voicer Questel | 24 |
| Olive Oyl's brother | 23 |
| Olive Oyl's creator | 23 |
| Olive Oyl's creator Elzie | 29 |
| Olive Oyl's mother | 22 |
| Olive that's very thin | 26 |
| Olive tree's relative | 25 |
| Olive with a little salt? | 25 |
| Olive with hardly any fat | 25 |
| Olive __ (army uniforms) | 24 |
| Olive __ (military uniform) | 27 |
| Olive __: uniform color | 23 |
| Olive ___ (army color) | 22 |
| Olive ___ (Army uniforms) | 25 |
| Olive ___ (military color) | 26 |
| Olive ___ (Popeye's gal) | 28 |
| Olive ___ (Popeye's lady) | 29 |
| Olive ___ (Popeye's love) | 29 |
| Olive ___ (uniform color) | 25 |