| Text | Length |
| Old Oldses | 10 |
| Old Oldsmobile | 14 |
| Old Oldsmobile competitors | 26 |
| Old Oldsmobiles | 15 |
| Old Olympic swimmer Gertrude | 28 |
| Old Olympics award | 18 |
| Old one | 7 |
| Old one, along the Oder | 23 |
| Old one, in Aachen | 18 |
| Old one, in Austria | 19 |
| Old one, in German | 18 |
| Old one, in Oldenburg | 21 |
| Old one: Ger. | 13 |
| Old ones are crocks | 19 |
| Old ones die hard, they say | 27 |
| Old ones: Abbr. | 15 |
| Old operating room substance | 28 |
| Old operating-room substance | 28 |
| Old Opry network | 16 |
| Old or morning follower | 23 |
| Old or New | 10 |
| Old or New follower | 19 |
| Old or Pete | 11 |
| Old or road follower | 20 |
| Old or top | 10 |
| Old or trick ending | 19 |
| Old or vain | 11 |
| Old or young follower | 21 |
| Old orchard spray | 17 |
| Old orchestral string | 21 |
| Old orchestral stringed instrument | 34 |
| Old orgy cry | 12 |
| Old Orkney land unit | 20 |
| Old Orly jet | 12 |
| Old oscilloscope part, briefly | 30 |
| Old OTC watchdog | 16 |
| Old Ottoman governor | 20 |
| Old Ottoman leaders | 19 |
| Old Ottoman title | 17 |
| Old Ottoman VIPs | 16 |
| Old outhouse | 12 |
| Old Overholt, e.g. | 18 |
| Old overlord | 12 |
| Old overlords | 13 |
| Old pageant name | 16 |
| Old pager signals | 17 |
| Old Paint, for example | 22 |
| Old pair | 8 |
| Old pal | 7 |
| Old PAlestinian letter | 22 |
| Old Palm phone | 14 |
| Old Palm smartphone | 19 |
| Old Pan Am rival | 16 |
| Old pantry supply | 17 |
| Old pantyhose brand with a famous Joe Namath ad | 47 |
| Old paper | 9 |
| Old paper currency | 18 |
| Old paper part | 14 |
| Old paper parts | 15 |
| Old paper section | 17 |
| Old paperboy's cry | 22 |
| Old parachute fabric | 20 |
| Old Paris landmark | 18 |
| Old Paris newspaper, with "Le" | 40 |
| Old Parisian money | 18 |
| Old Parisian smackers | 21 |
| Old Parmesan bread? | 19 |
| Old part-song | 13 |
| Old partner of Rodgers | 22 |
| Old partners | 12 |
| Old party | 9 |
| Old patriarch | 13 |
| Old pawnshop feature | 20 |
| Old PC component | 16 |
| Old PC display | 14 |
| Old PC display device | 21 |
| Old PC display part | 19 |
| Old PC installation | 19 |
| Old PC interface | 16 |
| Old PC monitor | 14 |
| Old PC monitor type | 19 |
| Old PC monitors | 15 |
| Old PC operating system | 23 |
| Old PC part | 11 |
| Old PC platform | 15 |
| Old PC screen | 13 |
| Old PC screens | 14 |
| Old PC software | 15 |
| Old PC standard | 15 |
| Old PD alert | 12 |
| Old PDA brand that fittingly fit in your hand | 45 |
| Old Peculier, for one | 21 |
| Old Peking weight | 17 |
| Old pen | 7 |
| Old pen parts | 13 |
| Old people of Gaul | 18 |
| Old Peppermint Lounge dance | 27 |
| Old Persian capital | 19 |
| Old Persian cohort | 18 |
| Old Persian coin | 16 |
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