| IDIE | "And When ?" (1969 hit) |
| OBLONGBOX | The ?, 1969 horror film starring Vincent Price and Christopher Lee (6,3) |
| WILDBUNCH | The ?, 1969 action film starring William Holden and Ernest Borgnine (4,5) |
| STEWART | Jackie ?, 1969, 1971 and 1973 F1 world drivers' championship winner |
| OLIVARES | Ruben ?, 1969-70 and 1971-72 undisputed World Bantamweight boxing champion |
| INTHEYEAR2525 | Deejay's thought about when rushhour traffic might actually rush? (1969) |
| MADBOONERISING | Frontiersman awakening in a foul mood? [1969] |
| PROCESS | The ?, 1969 novel by Brion Gysin (7) |
| MOODY | Orville ?, 1969 US Open golf champion (5) |
| NIHILL | Paul ?, 1969 European Championships 20k walk gold medallist (6) |
| BOARD | Lillian ?, 1969 European Championships 800m gold medallist (5) |
| STUD | The ?, 1969 novel by Jackie Collins (4) |
| ESTATE | The ?, 1969 novel by Isaac Bashevis Singer (6) |
| GREEN | The ?, 1969 novel by Kingsley Amis (5,3) |
| SUSPICIOUSMINDS | Possible requirement of postal inspectors? (1969) |
| SIXTHSEAL | The ?, 1969 novel by Mary Wesley |
| LAVER | Rod ?, 1969 Wimbledon men's singles tennis championship winner |
| SPINNINGWHEEL | Deejay's problem after flooring it? (1969) |
| SPUNSUGAR | Listened to a record by the Archies? (1969) |
| MAN | The ?, 1969 novel by Kingsley Amis (5,3) |
