From the reports I’ve read (I was not able to catch it live), Round One?goes to Allen:

During the debate, Allen tried to needle Webb, a novelist who has also worked on feature films in Hollywood. Allen spoke of pursuing “Virginia values” instead of “Hollywood values” and made several references to Webb’s writing career.

At one point, in reference to a question about the Guantanamo Bay prison, Webb spoke of a book he wrote that mentioned detainees after World War II. Allen responded by saying that he had visited Guantanamo Bay. “That is the real world. That is not a book,” Allen said.

Allen’s campaign had said it wanted to highlight Webb’s lack of knowledge on issues facing Virginia.

A half-hour into the debate, Allen caught the challenger off guard by asking him a question that forced Webb to admit he was unfamiliar with Portsmouth’s Craney Island, which consists of dredged material that officials hope to turn into a cargo terminal.

“Craney Island is in Virginia,” said Allen, who then lectured Webb about the site. “I got it, George. I got it, George,” Webb responded.