Andy Roddick Retiring: The 10 Greatest Moments of His Storied Tennis Career

For the majority of his career, Andy Roddick was the top-ranked American player in tennis. Furthermore, in spite of his often ornery personality, he was very popular with American tennis fans.

Roddick won the 2003 U.S. Open, and if not for his four finals losses in Grand Slams to world No. 1 Roger Federer, he might be considered one of the sport's true greats.

10. 2003 Montreal Masters

Roddick captured his first Masters Series title by winning in Canada. He came from behind in the decisive third set to beat Federer in the semifinal, which for a while was Roddick’s only career victory over the Swiss star.

9. 2009 Australian Quarters

Roddick had dropped only one set through his first four rounds before meeting defending champion Novak Djokovic in the quarterfinals of the 2009 Australian Open.

After dropping the first set in a tiebreak, Roddick took the next two sets.

Trailing two-sets-to-one and 2-1 in the fourth, Djokovic retired due to heat exhaustion. Despite the anticlimactic end, it remains one of the biggest victories of his career. 

8. 2009 Wimbledon Semifinal

Roddick upset Andy Murray in four sets, once again thwarting the hopes and dreams of the British tennis fans.

Roddick won 6-4, 4-6, 7-6, 7-6. He won the tiebreaks 9-7 and 7-5, and set the stage for what some consider the greatest match ever played.

7. 2012 Miami Masters Victory over Federer

Although it was only the third round, defeating Federer for just the third time in 24 career matches was a big accomplishment for Roddick at this point in his career.

They split the first two sets, before Roddick took advantage of a late break of serve to defeat his longtime nemesis.

As with many matches throughout his career, Roddick was unable to take advantage of the opportunity in front of him. He later lost 7-5, 6-0 to Juan Monaco. 

6. 2003 US Open Semifinal

Roddick overcame a two-set deficit against David Nalbandian to advance to his first Grand Slam final.

The American won a tight third set tiebreak 9-7, before taking the following sets 6-3, 6-1 to advance to the biggest match of his career at that time. 

5. 2007 Davis Cup Victory

Roddick anchored the Davis Cup throughout most of his career, and got the U.S. off to a good start in the finals against Russia in 2007.

Playing first, Roddick ousted Dmitry Tursunov in straight sets to give the Americans a 1-0 lead. James Blake won the next match for the U.S. to put them 2-0 up. The Bryan brothers' ensuing victory in doubles gave the U.S. its first Davis Cup win in 12 years. 

4. 2003 Year End No. 1

At just 21, Roddick had the best year of his career in 2003.

In addition to winning the U.S. Open, Roddick also advanced to the semifinals in Australia and at Wimbledon. 

3. 2003 Australian Open Win over El-Aynaoui

Seeded ninth, Roddick had to come back from two sets down to defeat Mikhail Youzhny in the fourth round. 

Roddick’s 21-19 fifth set victory over Younes El-Aynaoui in the quarterfinals set the record for the longest fifth set until the epic Isner-Mahut match at Wimbledon in 2010.

The win advanced Roddick to his first Grand Slam semifinal and set the stage for the best year of his career. 

2. 2003 US Open Championship

Coming off an emotional comeback in the semifinal, Roddick defeated Juan Carlos Ferrero 6-3, 7-6, 6-3.

Roddick had won his first Grand Slam title at age 21, and seemed to set the stage for the first of many.

Instead, it is likely to be the only of his career.

The victory vaulted Roddick to the No. 1 ranking in the world. To this day, he remains the last American men's tennis player to be ranked No. 1 and the last American to finish the year ranked No. 1 as well.

He also became the youngest American to be ranked No. 1.

1. 2009 Wimbledon Final Loss to Federer

It is not often that an athlete can proclaim that one of his or her greatest moments was in defeat.

The guts and determination that Roddick showed in a heart-wrenching loss to Roger Federer in the Wimbledon final in 2009 earned him more respect than most of his wins. 

Roddick won the first set and then took a 6-2 lead in the second set tiebreak. However, he was unable to convert any of his four set points.

This is the moment that most point to as the turning point of the match.

Federer won the final six points of the second set to even the match. He then won the third set 7-5 in another tiebreak. However, Roddick captured the fourth set to set up an epic fifth.

Of course, Roddick eventually lost the match despite being broken only in the match's final game. 

Federer’s victory earned him his sixth Wimbledon title and 15th Grand Slam to break Pete Sampras’ record. It was also Roddick’s fourth loss to Federer in a Grand Slam final. Federer finally broke Roddick in the 30th game of the final set to win.