Doug Flach was always Ken's brother. Until he became the guy who upset Agassi in the first round of Wimbledon. 

Coached by his older brother Rick, he became a junior champion in St. Louis and the Missouri Valley, then an All-American at the University of Tennessee. At the Nick Bollettieri Tennis Academy in Bradenton, he roomed with Andre Agassi and Jim Courier. 

On June 24, 1996, ranked No. 108, Flach walked onto the grass at Wimbledon and beat his old roommate — a former Wimbledon and US Open champion. It's still considered one of the biggest first-round upsets in Wimbledon history. 

"The Wimbledon victory over Agassi was kind of my 15 minutes of fame," Doug said. He didn't even know HBO was broadcasting it back home. "So many people saw that match. It was a big deal for a day or two in the tennis world and the sports world, I guess. It's something people always want to talk about. It never dies." 

It was his biggest upset. It wasn't his only one. 

Three years earlier, he'd beaten Ivan Lendl at the Cincinnati Masters — winding down by then, but still Lendl. Two weeks later, he beat a nobody named Patrick Rafter in the first round of the US Open. Four years after that, Rafter won back-to-back US Opens. After Wimbledon, Flach beat Agassi again, then knocked off a qualifying-round Thomas Johansson, a future Australian Open champion, and took down French Open winner Gustavo Kuerten on clay in Amsterdam. At the 1998 Queen's Club Championships, he came in as an unseeded qualifier and beat fifth-seeded Karol Kucera on his way to the quarterfinals. On grass. As a qualifier. 

In doubles, he and Jim Courier beat John McEnroe and Goran Ivanisevic at Wimbledon in 1991, reaching the third round. Flach went on to win two ATP doubles titles, partnering with Paul Annacone and Sandon Stolle. 

His career-high singles ranking was No. 108. He's happy with that. 

"Tennis is difficult for a lot of people to understand," he said. "If I was the 100th-ranked tennis player in the world, people who don't really know tennis are like, 'Oh, that's too bad. Maybe next time you can get ranked higher or something.' Being the 100th-ranked tennis player in the world, it was very cool. I couldn't be happier with how I did." 

Lendl, Agassi, Rafter, Kuerten, Johansson, Kucera, McEnroe, and Ivanisevic might disagree. 

(2002)