| Old Sinclair Oil rival | 22 |
| Old silver coins of Spain | 25 |
| Old silver coins | 16 |
| Old silver coin of Italy | 24 |
| Old silver amts. | 16 |
| Old silo missile | 16 |
| Old Silk Road destination | 25 |
| Old Silk Road city in Kyrgyzstan | 32 |
| Old silk brocade | 16 |
| Old Sienese coin | 16 |
| Old sideshow attraction | 23 |
| Old Sicilian coin | 17 |
| Old Siamese coins: Var. | 23 |
| Old Siamese coin | 16 |
| Old shrimp has one | 18 |
| Old show-saver | 14 |
| Old show featuring the Schmenge Brothers polka band | 51 |
| Old shoulder gun | 16 |
| Old shortstop Marion's nickname | 35 |
| Old shopping locale | 19 |
| Old shopping centers | 20 |
| Old shoe polish brand | 21 |
| Old shoe accessory | 18 |
| Old shirt, maybe | 16 |
| Old shipping nickname | 21 |
| Old shipping moniker | 20 |
| Old shipping allowances | 23 |
| Old shipping allowance | 22 |
| Old shippable shelter | 21 |
| Old shipbuilding needs | 22 |
| Old ship's cargo | 20 |
| Old ship cradle | 15 |
| Old shields | 11 |
| Old shield | 10 |
| Old Sherman Hemsley sitcom | 26 |
| Old sheriff's badge | 23 |
| Old Shell rival | 15 |
| Old Shaker leader | 17 |
| Old sewing machine part | 23 |
| Old sewing machine mechanism | 28 |
| Old settings for many out-of-tune pianos | 40 |
| Old serving aid | 15 |
| Old service station name | 24 |
| Old servant's phrase of address | 35 |
| Old serf | 8 |
| Old Serbian capital | 19 |
| Old Serbian auto | 16 |
| Old senator's coverup | 25 |
| Old senate attire | 17 |
| Old seminar subject | 19 |
| Old self-titled talk show | 25 |
| Old self-realization program (abbr.) | 36 |
| Old self-realization program | 28 |
| Old seed making a court divider? | 32 |
| Old security device | 19 |
| Old section of Asia Minor | 25 |
| Old section of Algiers | 22 |
| Old section in Algiers | 22 |
| Old seaman | 10 |
| Old sea-war vessels | 19 |
| Old sea serpent | 15 |
| Old scrolls, often | 18 |
| Old screen star Lamarr | 22 |
| Old screen siren West | 21 |
| Old Scratch's delight | 25 |
| Old Scratch | 11 |
| Old scoundrel | 13 |
| Old Scottish landowners | 23 |
| Old Scottish landholder | 23 |
| Old Scottish county on the Clyde | 32 |
| Old Scottish coins | 18 |
| Old science magazine | 20 |
| Old science lab equipment | 25 |
| Old science issue | 17 |
| Old science fiction magazine | 28 |
| Old schoolteacher | 17 |
| Old schoolmistress | 18 |
| Old schoolmasters' sticks | 29 |
| Old schoolhouse item | 20 |
| Old school-desk items | 21 |
| Old school singer/actress Shore | 31 |
| Old school rapper Big Daddy ___ | 31 |
| Old school rapper Base | 22 |
| Old school punisher | 19 |
| Old school pronoun | 18 |
| Old school method | 17 |
| Old school machine | 18 |
| Old school item | 15 |
| Old school instruction | 22 |
| Old school hip-hop singer ___ Base | 34 |
| Old school gaming platform, for short | 37 |
| Old school figures | 18 |
| Old school figure | 17 |
| Old school desk's supply | 28 |
| Old school dance | 16 |
| Old school crooner Jackie | 25 |
| Old school copy | 15 |
| Old school board | 16 |
| Old school attachment? | 22 |
| Old school addition? | 20 |