I could find little in the way of biographical information about him after a half-hearted Web search. London's National Portrait Gallery has only this: "Thomas Cantrell Dugdale was a painter and book illustrator. During the First World War he served as a Staff Sergeant in the Middlesex Yeomanry." The Tate offers only a little more here.
As a result, we are left to fall upon the device of examining Dugdale's art. Which is a sensible thing to do, because that's what really counts.
Dugdale served in Allenby's Palestine campaign, though apparently not with the Buckinghamshire Hussars. As for the World War 2 scene, I have no information as to whether or not he had any sort of official war artist status.
This image might be an illustration, rather than strictly a painting.
An interesting, naturalistic pose. I wouldn't be surprised to learn that it was based on photography.
Stylistically different from Dugdale's other works, but another natural pose.
Dugdale seems to have painted quite a few portraits of British actresses during the 1930s, though I have no information regarding why.
I think Dugdale at his best was a good artist, yet not top-notch. I like the paintings of the mother-and-child and Andaluza best of this lot. The rest display a touch of Modernism that is manifested in a sort of dabby style that lacks punch and individuality. That might be why he is little remembered even though representational art is regaining popularity.