| Old-time desk accessory | 23 |
| Old-time desk features | 22 |
| Old-time double-dealer | 22 |
| Old-time farmers' rides | 27 |
| Old-time fountain employee | 26 |
| Old-time fountain worker | 24 |
| Old-time gangster movie actor | 29 |
| Old-time gossip queen Maxwell | 29 |
| Old-time humorist Bill | 22 |
| Old-time jail for deadbeats | 27 |
| Old-time Japanese governor | 26 |
| Old-time journalist Bugs | 24 |
| Old-time journalist-socialite | 29 |
| Old-time kitchen warmer | 23 |
| Old-time leading lady Dolores | 29 |
| Old-time merchant guild | 23 |
| Old-time motoring monogram | 26 |
| Old-time movie mogul Marcus | 27 |
| Old-time movie vamp Pola | 24 |
| Old-time newsman Sevareid | 25 |
| Old-time peep show venue | 24 |
| Old-time pianist Templeton | 26 |
| Old-time poacher deterrents | 27 |
| Old-time punishment need | 24 |
| Old-time radio crimefighter | 27 |
| Old-time railroad worker | 24 |
| Old-time sailor's drink | 27 |
| Old-time schoolroom adjunct | 27 |
| Old-time schoolteacher | 22 |
| Old-time security system | 24 |
| Old-time sidewalk show | 22 |
| Old-time singer Julius | 22 |
| Old-time singer Sir Harry | 25 |
| Old-time socialite Maxwell | 26 |
| Old-time soprano Lehmann | 24 |
| Old-time street fixture | 23 |
| Old-time street illuminator | 27 |
| Old-time telephone feature | 26 |
| Old-time transportation | 23 |
| Old-time Turkish title | 22 |
| Old-time whaler's harvest | 29 |
| Old-time word of reproach | 25 |
| Old-time Yankee great Chase | 27 |
| Old-timer in Wiesbaden | 22 |
| Old-Timers' Day celeb | 25 |
| Old-timey "not" | 25 |
| Old-timey after-school drink | 28 |
| Old-timey clock topper | 22 |
| Old-timey cobbler's need | 28 |
| Old-timey cries of distress | 27 |
| Old-timey detergent form | 24 |
| Old-timey film channel | 22 |
| Old-timey weather predictor | 27 |
| Old-timey words of emphasis | 27 |
| Old-West mode of travel | 23 |
| Old-___ (like a spinster) | 25 |
| Old-___-beard (green lichen) | 28 |
| Olde tyme "Listen!" | 29 |
| Olden times, in olden times | 27 |
| Olden Venetian magistrates | 26 |
| Oldenburg "oh!" | 25 |
| Older brother of Moses | 22 |
| Older name for a Swiss city | 27 |
| Older name of a Swiss city | 26 |
| Older titles, to a publisher | 28 |
| Older type of computer screen | 29 |
| Oldest Brady Bunch kid | 22 |
| Oldest British service branch | 29 |
| Oldest brother in Hanson | 24 |
| Oldest Cabinet department | 25 |
| Oldest city in Colombia | 23 |
| Oldest desert in the world | 26 |
| 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 |