| Text | Length |
| On shaky ground | 15 |
| On shank's mare | 19 |
| On sheltered side | 17 |
| On ship | 7 |
| On short notice | 15 |
| On sick leave | 13 |
| On skid row | 11 |
| On Soc. Sec. | 12 |
| On Soc. Sec., maybe | 19 |
| On Soc. Sec., often | 19 |
| On Soc. Sec., perhaps | 21 |
| On Soc. Sec., say | 17 |
| On Soc. Sec., typically | 23 |
| On Soc. Security, say | 21 |
| On Social Sec. | 14 |
| On Social Sec., say | 19 |
| On Social Security, say: Abbr. | 30 |
| On Social Security, typically (abbr.) | 37 |
| On Social Security: Abbr. | 25 |
| On solid ground | 15 |
| On some naval maneuvers, e.g. | 29 |
| On some roads, it might be several miles after the last one | 59 |
| On something | 12 |
| On something? | 13 |
| On spring's fringe? | 23 |
| On SS, maybe | 12 |
| On SS, perhaps | 14 |
| On stage by herself | 19 |
| On stage in the cast | 20 |
| On strike | 9 |
| On strike, say | 14 |
| On sudden impulse | 17 |
| On Sunset Blvd., say | 20 |
| On t'other side | 19 |
| On tap | 6 |
| On target | 9 |
| On task | 7 |
| On tenterhooks | 14 |
| On terra -- | 11 |
| On terra firma | 14 |
| On that account | 15 |
| On that spot | 12 |
| On the "Index Librorum Prohibitorum" | 46 |
| On the "Queen Mary 2", maybe | 38 |
| On the -- (at risk of exclusion) | 32 |
| On the -- (at variance) | 23 |
| On the -- (discreetly) | 22 |
| On the -- (escaping) | 20 |
| On the -- (fleeing) | 19 |
| On the -- (hiding out) | 22 |
| On the -- (unfriend-ly) | 23 |
| On the -- of (close to) | 23 |
| On the -- vive | 14 |
| On the --- (fleeing) | 20 |
| On the --- (precisely) | 22 |
| On the --- (watchful) | 21 |
| On the --- vive | 15 |
| On the 31st of February | 23 |
| On the A-list | 13 |
| On the Adriatic | 15 |
| On the Adriatic, say | 20 |
| On the Aegean | 13 |
| On the Aegean, e.g. | 19 |
| On the Aegean, say | 18 |
| On the affirmative side | 23 |
| On the agenda | 13 |
| On the alert | 12 |
| On the Andaman | 14 |
| On the apex | 11 |
| On the apex of | 14 |
| On the Aral | 11 |
| On the ascendant | 16 |
| On the Atlantic | 15 |
| On the Atlantic or Pacific | 26 |
| On the Atlantic, e.g. | 21 |
| On the Atlantic, say | 20 |
| On the authority of | 19 |
| On the Azov | 11 |
| On the back | 11 |
| On the back at work, it's good; on the backside at work, it's bad | 73 |
| On the back burner, perhaps | 27 |
| On the back, as a fin | 21 |
| On the bad side (of) | 20 |
| On the ball | 11 |
| On the ball or on the dot | 25 |
| On the ball, in a way | 21 |
| On the Baltic | 13 |
| On the Baltic, say | 18 |
| On the Barents | 14 |
| On the beach | 12 |
| On the best of terms | 20 |
| On the best-dressed list | 24 |
| On the bias | 11 |
| On the Big Board | 16 |
| On the big drink | 16 |
| On the Black | 12 |
| On the black market, most likely | 32 |
| On the Black or Red | 19 |
| On the blink | 12 |
| On the block | 12 |
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