| Text | Length |
| On the verge of doing it | 24 |
| On the verge of a meltdown | 26 |
| On the verge of | 15 |
| On the verge | 12 |
| On the upturn | 13 |
| On the upswing | 14 |
| On the up-and-up? | 17 |
| On the up-and-up, so to speak | 29 |
| On the up-and-up, morally | 25 |
| On the up-and-up | 16 |
| On the up ___ | 13 |
| On the up side | 14 |
| On the up and up | 16 |
| On the Tyrrhenian, e.g. | 23 |
| On the train | 12 |
| On the trail of | 15 |
| On the trail (of) | 17 |
| On the track once again? | 24 |
| On the town | 11 |
| On the topic of, briefly | 24 |
| On the topic of | 15 |
| On the throne | 13 |
| On the team? | 12 |
| On the tarmac | 13 |
| On the take | 11 |
| On the tail of | 14 |
| On the swarthy side | 19 |
| On the surface? | 15 |
| On the surface, measurably | 26 |
| On the surface of | 17 |
| On the surface | 14 |
| On the sundeck | 14 |
| On the summit of | 16 |
| On the summit | 13 |
| On the subject of | 17 |
| On the stump | 12 |
| On the stove | 12 |
| On the stock exchange | 21 |
| On the statuesque side | 22 |
| On the square | 13 |
| On the spot | 11 |
| On the Spanish Main | 19 |
| On the sordid side | 18 |
| On the small side | 17 |
| On the sly | 10 |
| On the slopes | 13 |
| On the skids | 12 |
| On the sidelines, maybe | 23 |
| On the sidelines | 16 |
| On the side of | 14 |
| On the side (of) | 16 |
| On the side | 11 |
| On the sick list | 16 |
| On the shore | 12 |
| On the ship, e.g. | 17 |
| On the ship | 11 |
| On the sheltered side | 21 |
| On the seas: Abbr. | 18 |
| On the search for baby apparel? | 31 |
| On the sea | 10 |
| On the schedule | 15 |
| On the say-so of | 16 |
| On the Sargasso | 15 |
| On the same ___ (in sync) | 25 |
| On the same ___ (in rapport) | 28 |
| On the same wavelength | 22 |
| On the same team (with) | 23 |
| On the same side, in war | 24 |
| On the same side as | 19 |
| On the same side | 16 |
| On the same page, so to speak | 29 |
| On the same page | 16 |
| On the same level | 17 |
| On the same family tree | 23 |
| On the salt water | 17 |
| On the safer side at sea | 24 |
| On the safer side | 17 |
| On the safe side? | 17 |
| On the safe side, nautically | 28 |
| On the safe side, at sea | 24 |
| On the safe side | 16 |
| On the run | 10 |
| On the roster | 13 |
| On the ropes | 12 |
| On the roof of | 14 |
| On the roof | 11 |
| On the rolls | 12 |
| On the rocks, in a bar | 22 |
| On the rocks, as tea | 20 |
| On the rocks | 12 |
| On the road, perhaps | 20 |
| On the road, in sports | 22 |
| On the road | 11 |
| On the rise | 11 |
| On the right: Fr. | 17 |
| On the right track | 18 |
| On the right half of the no. line | 33 |
| On the right and left | 21 |
| On the right | 12 |
| On the Red or Yellow | 20 |
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