Andy Roddick played some of his best tennis at the US Open over the years, winning his sole Major title at the event.
The American ATP legend played 55 matches at Flushing Meadows throughout his career, coming out on top 43 times.
Seven of those 43 victories came in 2003, as Roddick beat Juan Carlos Ferrero in straight sets to win the US Open title.
Nine years later, Roddick lost to Juan Martin del Potro in the fourth round of the US Open, his final-ever singles match as a professional.
Looking back in 2020, Roddick named one US Open match as the most shocking in tennis history.
Andy Roddick once said Roberta Vinci’s US Open win over Serena Williams was the biggest upset ever
Appearing as an analyst on the Tennis Channel five years ago, Roddick was asked whether he agreed Serena Williams’ defeat to Roberta Vinci at the US Open in 2015 was the most shocking result in the history of the sport.
“Yeah,” said Roddick.
“Serena Williams, you had it, winning three Slams coming in, in form coming in.
“The other thing is, she doesn’t win the first set and lose very often, all of these factors with Serena, the history at the venue, experience, everything you would want was in her corner, and nothing about the [Roberta] Vinci win, besides her playing a very smart, strategic match and using what she had, made any sense.
“I’m not mad at anyone who thinks that’s one of the biggest [upsets] ever.”
Williams was a heavy favorite heading into the semi-final, having won her previous 26 matches at the US Open.
The American was also chasing the elusive Calendar Grand Slam, following her victories at the Australian Open, French Open, and Wimbledon earlier in the year.
- 2015 Australian Open F – Serena Williams beat Maria Sharapova, 6-3, 7-6
- 2015 French Open F – Serena Williams beat Lucie Safarova, 6-3, 6-7, 6-2
- 2015 Wimbledon F – Serena Williams beat Garbine Muguruza, 6-4, 6-4
She couldn’t quite get over the line, however, as she lost to Vinci in the semi-finals, 6-2, 4-6, 4-6.
Vinci’s win was ranked first in a list of the top ten all-time Grand Slam upsets, and while Roddick had no problem with her place at number one, he did take issue with the fifth-placed match.
| Rank | Tournament/Round | Winner | Loser | Score |
| 1 | 2015 US Open – SF | Roberta Vinci | Serena Williams | 2-6, 6-4, 6-4 |
| 2 | 2009 French Open – 4R | Robin Soderling | Rafael Nadal | 6-2, 6-7, 6-4, 7-6 |
| 3 | 1983 French Open – 4R | Kathy Horvath | Martina Navratilova | 6-4, 0-6, 6-3 |
| 4 | 1994 Wimbledon – 1R | Lori McNeil | Steffi Graf | 7-5, 7-6 |
| 5 | 2002 Wimbledon – 2R | George Bastl | Pete Sampras | 6-3, 6-2, 4-6, 3-6, 6-4 |
| 6 | 1975 Wimbledon – F | Arthur Ashe | Jimmy Connors | 6-1, 6-1, 5-7, 6-4 |
| 7 | 1987 Wimbledon – 2R | Peter Doohan | Boris Becker | 7-6, 4-6, 6-2, 6-4 |
| 8 | 2013 Wimbledon – 2R | Sergiy Stakhovsky | Roger Federer | 6-7, 7-6, 7-5, 7-6 |
| 9 | 2017 Australian Open – 2R | Denis Istomin | Novak Djokovic | 7-6, 5-7, 2-6, 7-6, 6-4 |
| 10 | 1989 French Open – 4R | Michael Chang | Ivan Lendl | 4-6, 4-6, 6-3, 6-3, 6-3 |
“I’ve actually disagreed with a couple of points on the list, just because it didn’t take in [to account] form going into an event,” he said.
“The [Pete] Sampras, [George] Bastl match, Pete was searching that entire year almost; he hadn’t been playing well, his confidence was a little shaky.
“I know we give credit to the Wimbledon mystique around Pete, but at the end of the day, you have to show up ready to play on any given day.”
Andy Roddick picks the two biggest upset wins from his entire tennis career
The 42-year-old was then asked to name the biggest shock win from his time as a professional.
“I thought of two,” said Roddick.
“One was ‘01 in Miami against Pete [Sampras], I think I was ranked 140 in the world at the time, and he was ranked three.
“For me, getting rid of the cobwebs because you idolized someone and actually going to work is a hard thing to do.”
Roddick beat Sampras, 7-6, 6-3, to advance to the fourth round of the 2001 Miami Open.
The American then named another Miami Open victory, which he considered to be one of the most shocking of his career.
“My last year on tour, I was playing horrendously, and I spent my entire life playing really well and not beating Roger [Federer], and for like a two-week stretch, I beat him in an exhibition and I beat him in Miami.
“I was losing to everyone else and just beating Roger. You explain it to me, I don’t know how the hell it all works.”
Roddick beat Federer, 7-6, 1-6, 6-4, to secure just his third career victory against the 20-time Major champion.
Only time will tell if we are set to witness any more shocking results at Grand Slam events in 2025, but it’ll certainly be worth watching out for.
The 2025 French Open tournament is set to begin on Sunday, May 25.
Receive exclusive tennis news and updates twice a week to your mailbox
