| Old radio show | 14 |
| Old radio show with "The" | 35 |
| Old radio show, with "The" | 36 |
| Old radio title character | 25 |
| Old radio tube | 14 |
| Old radio word for the letter O | 31 |
| Old radio's "My Friend ___" | 41 |
| Old radio's "Vic and ___" | 39 |
| Old radio's "___ 'n' Andy" | 48 |
| Old radio's "___ Maxwell's Party Line" | 56 |
| Old radio's Digger ___ | 26 |
| Old radio's Fibber ___ | 26 |
| Old radio's Major ___ | 25 |
| Old radio's ___ Stoopnagle | 30 |
| Old ragtime dance | 17 |
| Old rail riders | 15 |
| Old railroad employee | 21 |
| Old railroad name | 17 |
| Old railroad showpieces | 23 |
| Old railway operator's hat | 30 |
| Old Rambler manufacturer | 24 |
| Old rapier | 10 |
| Old RCA classical music label | 29 |
| Old reception aid | 17 |
| Old reception aids | 18 |
| Old reciprocal electrical unit | 30 |
| Old recompense | 14 |
| Old record biz initials | 23 |
| Old record company | 18 |
| Old record holder | 17 |
| Old record label | 16 |
| Old record label's boat to reach isolated areas (if X=10)? | 62 |
| Old record material | 19 |
| Old record player | 17 |
| Old record players | 18 |
| Old record problem | 18 |
| Old recorder format | 19 |
| Old recording device | 20 |
| Old recording disk | 18 |
| Old recordings, for short | 25 |
| Old records | 11 |
| Old records for short | 22 |
| Old Red head, so to speak? | 26 |
| Old Red Scare grp. | 18 |
| Old red states?: Abbr. | 22 |
| Old reformist plan | 18 |
| Old refrain | 11 |
| Old region near Dead Sea | 24 |
| Old region of Asia Minor | 24 |
| Old relatives of the guitar | 27 |
| Old religious scandal inits. | 28 |
| Old remains | 11 |
| Old Remington competitor | 24 |
| Old Renault | 11 |
| Old republic letters | 20 |
| Old republican? | 15 |
| Old revolutionist | 17 |
| Old rhyme for hit | 17 |
| Old Richmond-based org. | 23 |
| Old riddle: "What did Delaware?" Answer: "I don't know, but ___" | 88 |
| Old rifle pin | 13 |
| Old ring king | 13 |
| Old ring king Muhammad | 22 |
| Old ring leader? | 16 |
| Old Ritz rival | 14 |
| Old rival of America | 20 |
| Old rival of Athens | 19 |
| Old rival of Google | 19 |
| Old rival of Life | 17 |
| Old rival of MGM | 16 |
| Old rival of Rutgers | 20 |
| Old rival of United | 19 |
| Old riverboats | 14 |
| Old road | 8 |
| Old road to Fairbanks | 21 |
| Old roadside advertiser | 23 |
| Old roadside name | 17 |
| Old roadster | 12 |
| Old Robert Blake cop show | 25 |
| Old rock collection | 19 |
| Old Rolling Stones record label | 31 |
| Old Roman arena fighter | 23 |
| Old Roman attire | 16 |
| Old Roman being | 15 |
| Old Roman chest | 15 |
| Old Roman coin | 14 |
| Old Roman coins | 15 |
| Old Roman council | 17 |
| Old Roman cry | 13 |
| Old Roman cuirass | 17 |
| Old Roman cup | 13 |
| Old Roman date | 14 |
| Old Roman dish | 14 |
| Old Roman dough | 15 |
| Old Roman festival: Apr. 28 | 27 |
| Old Roman garment | 17 |
| Old Roman gold coins | 20 |
| Old Roman gown | 14 |
| Old Roman greeting | 18 |
| Old Roman greetings | 19 |