| Text | Length |
| On a slow boat to China, e.g. | 29 |
| On a slow roller: "A Midsummer Night's Dream" | 59 |
| On a small scale | 16 |
| On a smaller scale | 18 |
| On a sofa | 9 |
| On a sofa, say | 14 |
| On a sortie | 11 |
| On a Spanish ship | 17 |
| On a spit, say | 14 |
| On a spree | 10 |
| On a steamer, say | 17 |
| On a streak | 11 |
| On a streak? | 12 |
| On a tandem, e.g. | 17 |
| On a tear | 9 |
| On a tether | 11 |
| On a tight schedule | 19 |
| On a tilt | 9 |
| On a train | 10 |
| On a vacation | 13 |
| On a vessel's left | 22 |
| On a voyage | 11 |
| On a voyage on the ocean | 24 |
| On a warpath | 12 |
| On a wayward path | 17 |
| On a windjammer | 15 |
| On a wing ___ prayer | 20 |
| On a winning streak | 19 |
| On a yacht, briefly | 19 |
| On a __-to-know basis | 21 |
| On a ___ | 8 |
| On a ___ (carousing) | 20 |
| On a ___ (raging) | 17 |
| On a ___-to-know basis | 22 |
| On account (of) | 15 |
| On account of | 13 |
| On account of (with ''to'') | 43 |
| ON address, or actress Lohan | 28 |
| ON address, or Disney duck | 26 |
| On again | 8 |
| On again, as a candle | 21 |
| On again, as a lantern | 22 |
| On again, in a way | 18 |
| On air icon | 11 |
| On air trucker? | 15 |
| On Alcatraz, e.g. | 17 |
| On alert | 8 |
| On all -- (crawling) | 20 |
| On all --- (crawling) | 21 |
| On all counts | 13 |
| On all sides | 12 |
| On all ___ (crawling, say) | 26 |
| On an ad -- basis | 17 |
| On an aimless course | 20 |
| On an airplane | 14 |
| On an America's Cup yacht | 29 |
| On an angle | 11 |
| On an annual basis | 18 |
| On an ark | 9 |
| On an ark, e.g. | 15 |
| On an ego trip | 14 |
| On an enforced diet of sorts | 28 |
| On an errand, maybe | 19 |
| On an errand, say | 17 |
| On an even --- | 14 |
| On an even keel | 15 |
| On an even __ (steady) | 22 |
| On an even ___ | 14 |
| On an even ___ (stable) | 23 |
| On an incline | 13 |
| On an ocean journey | 19 |
| On an ocean liner | 17 |
| On an ocean liner, e.g. | 23 |
| On an ocean liner, maybe | 24 |
| On an ocean liner, perhaps | 26 |
| On an ocean liner, say | 22 |
| On an ocean voyage | 18 |
| On an opponent's field | 26 |
| On an upswing | 13 |
| On an ___ basis | 15 |
| On and after | 12 |
| On and off | 10 |
| On and off items | 16 |
| On and on | 9 |
| On and on and on and ... | 24 |
| On and on and on and on and ... | 31 |
| On another planet | 17 |
| On any occasion | 15 |
| On balance | 10 |
| On base | 7 |
| On behalf of | 12 |
| On bended ___ | 13 |
| On board | 8 |
| On board direction | 18 |
| On board ship | 13 |
| On both banks of | 16 |
| On both sides | 13 |
| On both sides of | 16 |
| On both sides: Prefix | 21 |
| On break | 8 |
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