The wicked Hugo Baskerville’s story is told in colourful, indeed sensationalist terms, in the old manuscript that Dr Mortimer shows to Holmes. It seems that the legendary hell-hound that haunts the Baskerville family first appeared to Hugo, and killed him, presumably as punishment for his sins. Apparently, he was keeping a peasant girl prisoner and when she escaped, set off in hot pursuit. Some of his equally dissolute companions rode out after him. Eventually they found him, in the process of having his throat ripped out by the fearsome, supernatural hound:
There stood a foul thing, a great black beast like a hound, yet larger than any hound that ever mortal eye rested upon. (chapter 2)
This, then, is the confrontation of Hugo with the hound, and it seems to have been a wholly unequal contest.
Hugo, at least, got his just deserts. However, the hound has now seemingly surfaced in modern times and is threatening the present Baskerville heir, Sir Henry, who is of a very different cast to his wicked ancestor, being a pleasant and friendly individual. Nevertheless, he appears to have fallen under the same shadow.