| CAGED | Caught the old and imprisoned them (5) |
| CHEAP | Caught the old car going for a song (5) |
| BIBLE | The ?, collection of Christian scriptures consisting of the Old and New Testaments (5) |
| WORLDS | Wrestled Bowen out from being the old and the new? |
| THEMOUND | Slope in Edinburgh connecting the old and new towns (3,5) |
| WALLEDUP | Breaking law, gets taken before the beak and imprisoned |
| BETWEEN | Wrestled Bowen out from being the old and the new? (7,6) |
| NORTHBRIDGE | Structure built in 1897 to link the old and new towns of Edinburgh (5,6) |
| RICHARDII | Son of the Black Prince who reigned as Plantagenet king of England before being usurped by Henry Bolingbroke and imprisoned in Pontefract Castle (7,1,1) |
| DAMAGED | Angry about the old and injured (7) |
| YEN | The old and new foreign capital (3) |
| TOEHOLDS | The old and so decrepit climbers might need these (8) |
| MAN | Robert Redford film, "The Old - & the Gun" |
| FILE | Handout for the old and confused at end of queue (4) |
| INCARCERATED | In trouble, criminal leader gets arrested, judged and imprisoned |
| CONFINED | Cheat penalized financially and imprisoned (8) |
| FATHOMED | Understood and imprisoned myself at home dutifully (8) |
| HONORARY | Without duties or reward, neither coming between the old and grizzled (8) |
| DOLE | Hand-out for the old and confused at end of queue (4) |
| HISS | Alger, American state department official tried and imprisoned for perjury in 1950 (4) |
