Definition of "woebegone"

The 44-year-old Prokhorov, the second-richest man in Russia, is expected to assume control of the woebegone Nets within the next few weeks.

2010 April 27, Howard Beck, “Russian Billionaire Is White Knight for the Nets”, in The New York Times‎

Pen and Miss Bolton were hard by listening to the same concert, and the latter remarked, and Pen laughed at Mr. Foker’s woebegone face.Fanny asked what it was that made that odd-looking little man so dismal? “I think he is crossed in love!” Pen said.

1848 November – 1850 December, William Makepeace Thackeray, chapter 47, in The History of Pendennis. […], volumes (please specify |volume=I or II), London: Bradbury and Evans, […], published 1849–1850

When he was finished, as such, he was wringing wet, and now he had to edge and shimmy his way back, and with a most woebegone look, and everybody laughing, except the sad blond boy, and the Minnesotans roaring in the cab.

1957, Jack Kerouac, On the Road, Penguin, published 1976, page 29