| Text | Length |
| On the outs | 11 |
| On the outs (with) | 18 |
| On the outs with | 16 |
| On the outs with a relative? | 28 |
| On the outside | 14 |
| On the outside: Prefix | 22 |
| On the Pacific | 14 |
| On the path to great success | 28 |
| On the pathway of enticement | 28 |
| On the pathway of futility | 26 |
| On the patio | 12 |
| On the payroll | 14 |
| On the peak | 11 |
| On the peak of | 14 |
| On the perimeter | 16 |
| On the periphery | 16 |
| On the petite side | 18 |
| On the phone | 12 |
| On the picket line | 18 |
| On the pink side | 16 |
| On the pinnacle | 15 |
| On the pinnacle of | 18 |
| On the plane | 12 |
| On the plane, e.g. | 18 |
| On the planet | 13 |
| On the plump side | 17 |
| On the plus side?: Abbr. | 24 |
| On the podium did he say, "O, I can't sin!"? | 58 |
| On the portly side | 18 |
| On the pro side | 15 |
| On the protected side | 21 |
| On the prowl | 12 |
| On the prowl, perhaps | 21 |
| On the q.t. | 11 |
| On the QE2 | 10 |
| On the qui -- | 13 |
| On the qui vive | 15 |
| On the qui __: alert | 20 |
| On the qui ___ | 14 |
| On the qui ___ (watchful) | 25 |
| On the qui _____ | 16 |
| On the quiet | 12 |
| On the quiet side | 17 |
| On the quiet side, nautically | 29 |
| On the quiet side? | 18 |
| On the quieter side | 19 |
| On the racy side | 16 |
| On the range, say | 17 |
| On the rangy side | 17 |
| On the ready | 12 |
| On the receiving end of a Dear John letter | 42 |
| On the Red | 10 |
| On the Red or Black | 19 |
| On the Red or Dead | 18 |
| On the Red or the Dead | 22 |
| On the Red or Yellow | 20 |
| On the right | 12 |
| On the right and left | 21 |
| On the right half of the no. line | 33 |
| On the right track | 18 |
| On the right: Fr. | 17 |
| On the rise | 11 |
| On the road | 11 |
| On the road, in sports | 22 |
| On the road, perhaps | 20 |
| On the rocks | 12 |
| On the rocks, as tea | 20 |
| On the rocks, in a bar | 22 |
| On the rolls | 12 |
| On the roof | 11 |
| On the roof of | 14 |
| On the ropes | 12 |
| On the roster | 13 |
| On the run | 10 |
| On the safe side | 16 |
| On the safe side, at sea | 24 |
| On the safe side, nautically | 28 |
| On the safe side? | 17 |
| On the safer side | 17 |
| On the safer side at sea | 24 |
| On the salt water | 17 |
| On the same family tree | 23 |
| On the same level | 17 |
| On the same page | 16 |
| On the same page, so to speak | 29 |
| On the same side | 16 |
| On the same side as | 19 |
| On the same side, in war | 24 |
| On the same team (with) | 23 |
| On the same wavelength | 22 |
| On the same ___ (in rapport) | 28 |
| On the same ___ (in sync) | 25 |
| On the Sargasso | 15 |
| On the say-so of | 16 |
| On the schedule | 15 |
| On the sea | 10 |
| On the search for baby apparel? | 31 |
| On the seas: Abbr. | 18 |
| On the sheltered side | 21 |
| On the ship | 11 |
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