| On the Red or the Dead | 22 |
| On the Red or Dead | 18 |
| On the Red or Black | 19 |
| On the Red | 10 |
| On the receiving end of a Dear John letter | 42 |
| On the ready | 12 |
| On the rangy side | 17 |
| On the range, say | 17 |
| On the racy side | 16 |
| On the quieter side | 19 |
| On the quiet side? | 18 |
| On the quiet side, nautically | 29 |
| On the quiet side | 17 |
| On the quiet | 12 |
| On the qui _____ | 16 |
| On the qui ___ (watchful) | 25 |
| On the qui ___ | 14 |
| On the qui __: alert | 20 |
| On the qui vive | 15 |
| On the qui -- | 13 |
| On the QE2 | 10 |
| On the q.t. | 11 |
| On the prowl, perhaps | 21 |
| On the prowl | 12 |
| On the protected side | 21 |
| On the pro side | 15 |
| On the portly side | 18 |
| On the podium did he say, "O, I can't sin!"? | 58 |
| On the plus side?: Abbr. | 24 |
| On the plump side | 17 |
| On the planet | 13 |
| On the plane, e.g. | 18 |
| On the plane | 12 |
| On the pinnacle of | 18 |
| On the pinnacle | 15 |
| On the pink side | 16 |
| On the picket line | 18 |
| On the phone | 12 |
| On the petite side | 18 |
| On the periphery | 16 |
| On the perimeter | 16 |
| On the peak of | 14 |
| On the peak | 11 |
| On the payroll | 14 |
| On the patio | 12 |
| On the pathway of futility | 26 |
| On the pathway of enticement | 28 |
| On the path to great success | 28 |
| On the Pacific | 14 |
| On the outside: Prefix | 22 |
| On the outside | 14 |
| On the outs with a relative? | 28 |
| On the outs with | 16 |
| On the outs (with) | 18 |
| On the outs | 11 |
| On the other team's turf | 28 |
| On the other side of the street: Abbr. | 38 |
| On the other side of | 20 |
| On the other side | 17 |
| On the other hand, briefly | 26 |
| On the other hand | 17 |
| On the organist's mind | 26 |
| On the opposite side | 20 |
| On the opposite bank | 20 |
| On the open water | 17 |
| On the open ocean | 17 |
| On the open deck | 16 |
| On the offensive | 16 |
| On the ocean: Fr. | 17 |
| On the ocean or in a fog | 24 |
| On the ocean floor | 18 |
| On the ocean blue | 17 |
| On the ocean | 12 |
| On the observation deck, say | 28 |
| On the nose | 11 |
| On the newsstands | 17 |
| On the near side: Prefix | 24 |
| On the nasty side | 17 |
| On the move on the briny | 24 |
| On the move | 11 |
| On the mother-of-the-bride's mind | 37 |
| On the mother's side of the family | 38 |
| On the mother's side | 24 |
| On the Most Wanted list | 23 |
| On the money | 12 |
| On the modest side | 18 |
| On the mend, say, as one's arm | 34 |
| On the mend, in Munich | 22 |
| On the Mediterranean, e.g. | 26 |
| On the Mediterranean | 20 |
| On the mattress | 15 |
| On the matter of | 16 |
| On the maternal side | 20 |
| On the masts | 12 |
| On the Marmora | 14 |
| On the Marmara | 14 |
| On the market, in a way | 23 |
| On the market | 13 |
| On the mark | 11 |
| On the map | 10 |