| Old rapier | 10 |
| Old Rambler manufacturer | 24 |
| Old railway operator's hat | 30 |
| Old railroad showpieces | 23 |
| Old railroad name | 17 |
| Old railroad employee | 21 |
| Old rail riders | 15 |
| Old ragtime dance | 17 |
| Old radio's ___ Stoopnagle | 30 |
| Old radio's Major ___ | 25 |
| Old radio's Fibber ___ | 26 |
| Old radio's Digger ___ | 26 |
| Old radio's "___ Maxwell's Party Line" | 56 |
| Old radio's "___ 'n' Andy" | 48 |
| Old radio's "Vic and ___" | 39 |
| Old radio's "My Friend ___" | 41 |
| Old radio word for the letter O | 31 |
| Old radio tube | 14 |
| Old radio title character | 25 |
| Old radio show, with "The" | 36 |
| Old radio show with "The" | 35 |
| Old radio show | 14 |
| Old radio quiz show | 19 |
| Old radio parts | 15 |
| Old radio part | 14 |
| Old radio or TV part | 20 |
| Old radio format, for short | 27 |
| Old radio feature | 17 |
| Old radio favorite "Easy _____" | 41 |
| Old radio components | 20 |
| Old radio component | 19 |
| Old radio character | 19 |
| Old radio announcer Tony | 24 |
| Old quiz show category | 22 |
| Old queen's land | 20 |
| Old queen of Spain | 18 |
| Old Quechuan | 12 |
| Old quarter of Algiers | 22 |
| Old quarter | 11 |
| Old pyramid builder | 19 |
| Old pushcart cry | 16 |
| Old punisher | 12 |
| Old punch line? | 15 |
| Old pump sign | 13 |
| Old pump name | 13 |
| Old pump abbr. | 14 |
| Old pulpit | 10 |
| Old pulp magazine hero | 22 |
| Old pulp magazine | 17 |
| Old pulp fiction hero | 21 |
| Old public squares | 18 |
| Old public square | 17 |
| Old protest org. | 16 |
| Old protest grp. | 16 |
| Old prospector | 14 |
| Old pros | 8 |
| Old propaganda source | 21 |
| Old propaganda propagator | 25 |
| Old pronouns | 12 |
| Old pronoun | 11 |
| Old promenade | 13 |
| Old programming language | 24 |
| Old program featuring Brüno Gehard | 37 |
| Old profs | 9 |
| Old Procter & Gamble detergent | 34 |
| Old pro, perhaps | 16 |
| Old pro with good taste? | 24 |
| Old pro | 7 |
| Old Prizm maker | 15 |
| Old Prizm automaker | 19 |
| Old printing units | 18 |
| Old printing symbols | 20 |
| Old printing process, for short | 31 |
| Old printing machine | 20 |
| Old printer patterns | 20 |
| Old print | 9 |
| Old price scanner? | 18 |
| Old presser | 11 |
| Old press group | 15 |
| Old presidential inits. | 23 |
| Old preposition | 15 |
| Old prefix for while | 20 |
| Old prefix before "cello" | 35 |
| Old pre-op inhalant | 19 |
| Old prairie home material | 25 |
| Old powdered apparel | 20 |
| Old potentate | 13 |
| Old postcard tone | 17 |
| Old postcard cost | 17 |
| Old postal divisions | 20 |
| Old postal abbr. | 16 |
| Old post of the 7th Infantry Div. | 33 |
| Old possessive | 14 |
| Old Portuguese money | 20 |
| Old Portuguese currency | 23 |
| Old Portuguese coins: Var. | 26 |
| Old Portuguese coins | 20 |
| Old Portuguese coin | 19 |
| Old Portuguese bread | 20 |
| Old porticos | 12 |