The title came from the 1952 Hank Williams hit of the same name, although Robin Gibb said he had not heard of it. He added in 1000 UK #1 Hits by Jon Kutner and Spencer Leigh, "We absolutely thought that You Win Again was going to be a big hit. It took us a month to cut it and get the right mix."
It was a #1 single in Britain, Ireland, Switzerland, Germany, Austria and Norway, as well as making the top 10 in Italy, the Netherlands and Sweden. It also topped the Eurochart for 4 weeks. It was a major disappointment in the US however, only reaching #75 in the singles charts.
"You Win Again" was the lead single from their fifteenth album E.S.P., the group's first since 1981 (barring soundtrack contributions). It only reached #75 on the Billboard Hot 100, but became the group's fifth UK #1 — and their first chart-topper since 1979.
In 1989, the Bee Gees had a small comeback in the US with the Top 10 success of their single, "One." Their record company decided to capitalize on their new-found success and re-released "You Win Again." Yet again, the single did not generate enough interest to make a successful US chart run.