| JOWLS | Droopy facial features on Winston Churchill and bulldogs |
| HOUR | Film centring on Winston Churchill during World War II, Darkest ... (4) |
| SANDHURST | Common name for the Royal Military College in Camberley, Surrey, whose alumni include Sir Winston Churchill and Princes William and Harry (9) |
| SIRS | Winston Churchill and Paul McCartney |
| OLDMAN | Gary, who's played Winston Churchill and Sid Vicious (6) |
| GARYOLDMAN | Film actor whose roles have included Winston Churchill and Sid Vicious |
| HARROVIANS | Word used to describe the alumni of the school attended by Winston Churchill and Benedict Cumberbatch (10) |
| PIMLICO | Area neighbouring Belgravia in the City of Westminster, site of a number of blue plaques including those of Winston Churchill and Joseph Conrad (7) |
| EDEN | Sir Anthony -; prime minister preceded by Winston Churchill and succeeded by Harold Macmillan (4) |
| LAWRENCE | The Seven Pillars of Wisdom author painted by Augustus John who served as an advisor to Winston Churchill and later retreated to Clouds Hill in Dorset (8) |
| INSOMNIA | Sir Winston Churchill and Marilyn Monroe both suffered from what at night? (8) |
| POWERNAP | With notable partakers including Aristotle, Winston Churchill and Albert Einstein, a restorative snooze taken in the daytime (5,3) |
| ACHING | Hurting a facial feature on general |
| BEARD | Facial feature on a penny |
| LIP | Prominent facial feature on a pouty face |
| CHINK | Beam of light hit facial feature on king (5) |
| DARRYLBROHMAN | '80s Panthers and Bulldogs prop and "Big Marn" of The Footy Show (6,7) |
| REIMIS | Tyran Smith's son, Anthony Mundine's nephew and Bulldogs and Storm wing or centre (6) |
| NCAA | Org. with Huskies and Bulldogs |
| HALL | Ex-Saints, Swans and Bulldogs forward, 'Big Bad' Barry ... (4) |
