In 1989, Holmes defeated Todd Witsken 5–7, 6–4, 7–6(5), 4–6, 14–12 in the second round at Wimbledon, a match that was the longest men's singles match at Wimbledon timed at 5 hours 28 minutes until the epic Isner–Mahut match in 2010. During his seven-year career he twice beat Jimmy Connors and had wins over Andre Agassi, Aaron Krickstein, and Tim Mayotte.