| 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 |
| Oldest capital city in the United States | 40 |
| Oldest cable network | 20 |
| Oldest Cabinet department | 25 |
| Oldest brother in Hanson | 24 |
| Oldest British service branch | 29 |
| Oldest Brady daughter | 21 |
| Oldest Brady Bunch kid | 22 |
| Oldest Best Actress Oscar winner | 32 |
| Oldest Best Actress nominee (2012) | 34 |
| Oldest Beatle | 13 |
| Oldest basketball tourney in the U.S. | 37 |
| Oldest astronaut | 16 |
| Oldest annual 1/1 football game | 31 |
| Oldest animal-safety org. in the U.S. | 37 |
| Oldest and northernmost of the main Hawaiian islands | 52 |
| Oldest active NBAer | 19 |
| Oldest "The Brady Bunch" sister | 41 |
| Oldest "Brady Bunch" boy | 34 |
| Oldest | 6 |
| Older: Abbr. | 12 |
| Older, presumably | 17 |
| Older, perhaps | 14 |
| Older workers' advocacy gp. | 31 |
| Older women seeking younger men | 31 |
| Older woman's young lover, facetiously | 42 |
| Older woman's plaything, in slang | 37 |
| Older way to travel | 19 |
| Older type of computer screen | 29 |
| Older titles, to a publisher | 28 |
| Older than you | 14 |
| Older than jrs. | 15 |
| Older son of Isaac | 18 |
| Older society women | 19 |
| Older PC screens | 16 |
| Older partner? | 14 |
| Older partner | 13 |
| Older ones: Abbr. | 17 |
| Older name of a Swiss city | 26 |
| Older name for a Swiss city | 27 |
| Older kind of phone? | 20 |
| Older form of a word | 20 |
| Older folks | 11 |
| Older cousin of "Cool!" | 33 |
| Older couple's home, often | 30 |
| Older child, perhaps | 20 |
| Older chickens | 14 |
| Older but ___ | 13 |
| Older but __ | 12 |
| Older brother of Moses | 22 |
| Older brother of Michael Jackson | 32 |
| Older brother of designers Vasco and Rodolfo | 44 |
| Older and ___ | 13 |
| Older | 5 |
| Oldenburg outburst | 18 |
| Oldenburg exclamation | 21 |
| Oldenburg "oh!" | 25 |
| Olden: Abbr. | 12 |
| Olden warriors | 14 |
| Olden Venetian magistrates | 26 |
| Olden toilers | 13 |
| Olden times, in olden times | 27 |
| Olden times | 11 |
| Olden time | 10 |
| Olden old | 9 |
| Olden ointment | 14 |
| Olden meeting places | 20 |
| Olden magistrates | 17 |