| Old shoe polish brand | 21 |
| Old shopping centers | 20 |
| Old shopping locale | 19 |
| Old shortstop Marion's nickname | 35 |
| Old shoulder gun | 16 |
| Old show featuring the Schmenge Brothers polka band | 51 |
| Old show-saver | 14 |
| Old shrimp has one | 18 |
| Old Siamese coin | 16 |
| Old Siamese coins: Var. | 23 |
| Old Sicilian coin | 17 |
| Old sideshow attraction | 23 |
| Old Sienese coin | 16 |
| Old silk brocade | 16 |
| Old Silk Road city in Kyrgyzstan | 32 |
| Old Silk Road destination | 25 |
| Old silo missile | 16 |
| Old silver amts. | 16 |
| Old silver coin of Italy | 24 |
| Old silver coins | 16 |
| Old silver coins of Spain | 25 |
| Old Sinclair Oil rival | 22 |
| Old Sinclair rival | 18 |
| Old Singer parts | 16 |
| Old sit-in org. | 15 |
| Old sit-in stagers: Abbr. | 25 |
| Old sitcom | 10 |
| Old sitcom boy Taylor | 21 |
| Old sitcom character Dobie ___ | 30 |
| Old sitcom couple's surname | 31 |
| Old sitcom family | 17 |
| Old sitcom guy in Aarhus? | 25 |
| Old sitcom maid | 15 |
| Old sitcom mechanic, with "the" | 41 |
| Old sitcom sot | 14 |
| Old sitcom starring Walter Brennan | 34 |
| Old site of France's West Point | 35 |
| Old skating star Sonja | 22 |
| Old sketch comedy show | 22 |
| Old ski lift | 12 |
| Old ski lift contraption | 24 |
| Old skier's lift with a curved lower part | 45 |
| Old skirt part | 14 |
| Old slang for a 100-dollar bill | 31 |
| Old slang for a unique person | 29 |
| Old slang for something extraordinary | 37 |
| Old slangy ending for "yes" or "no" | 55 |
| Old slangy word of enthusiasm | 29 |
| Old slave | 9 |
| Old slavery class | 17 |
| Old Slavic group | 16 |
| Old Slavic title | 16 |
| Old sleep aid? | 14 |
| Old sleep inducer | 17 |
| Old sleep-inducer | 17 |
| Old sleeping aid? | 17 |
| Old slick magazine | 18 |
| Old snack cracker brand | 23 |
| Old sneaker feature | 19 |
| Old soap "___ Hope" | 29 |
| Old soap ingredient | 19 |
| Old soap ingredients | 20 |
| Old soap, perhaps | 17 |
| Old soap, sometimes | 19 |
| Old sobriquet for Wahlberg | 26 |
| Old sock feature | 16 |
| Old Sod | 7 |
| Old soda machine feature | 24 |
| Old sofa's problem | 22 |
| Old soft drink brand | 20 |
| Old Sol | 7 |
| Old Sol is one | 14 |
| Old Sol, diurnally | 18 |
| Old soldier | 11 |
| Old soldiers | 12 |
| Old soldiers' org. | 22 |
| Old song ''Abdul Abulbul ___'' | 46 |
| Old song "Abdul Abulbul ___" | 38 |
| Old song "_____ She Sweet?" | 37 |
| Old song done anew | 18 |
| Old song hit | 12 |
| Old song that goes "jing jing jing" | 45 |
| Old song title | 14 |
| Old song with the lyric "When he would ride in the afternoon / I'd follow him with my hickory broom" | 114 |
| Old song, "Mighty ___ a Rose" | 39 |
| Old Sony brand | 14 |
| Old Sony format | 15 |
| Old sorcerer | 12 |
| Old sound systems | 17 |
| Old source of news | 18 |
| Old source of stock reports | 27 |
| Old source of ticker tape | 25 |
| Old South | 9 |
| Old Southern estate | 19 |
| Old Southern fighters | 21 |
| Old sovereign | 13 |
| Old Soviet biggie | 17 |
| Old Soviet naval base site | 26 |
| Old Soviet news agcy. | 21 |
| Old Soviet news agency | 22 |