Roger Federer's 5 most challenging matches ft. Rafael Nadal, Andy Roddick

Roger Federer is widely regarded as one of the best players in the sport's history. The 41-year-old is renowned for his signature single-handed backhand and effortless style of play in the era of powerful double-handers.

Federer, who debuted on the ATP Tour in 1998, is calling time on his illustrious career at the Laver Cup this weekend. Having won 20 Majors, six ATP Finals, 28 Masters 1000s and numerous other titles, the Swiss has built a legacy that goes beyond numbers.

However, having not played since injuring his knee at Wimbledon last year, Federer dropped out of the ATP rankings a few weeks ago due to inactivity. Nevertheless, the Swiss maestro, who has a 1251-275 win-loss record, has had many an epic battle in some of the biggest matches of his career.

On that note, here's a look at the five toughest matches Roger Federer has been a part of over the years:

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#5. US Open 2011 SF: Novak Djokovic beats Roger Federer 6-7, 4-6, 6-3, 6-2, 7-5

Roger Federer lost to Djokovic in the US Open semifinals

A year after squandering match points in his US Open semifinal against Novak Djokovic, Roger Federer met the Serb once again with a place in the final at stake.

Determined to avoid a repeat of the fate from a year ago, the five-time champion made a bright start, taking the opener. Federer also took the second set to take a stranglehold of the match before Djokovic launched his comeback and forced a decider.

The Swiss maestro once again regained control of proceedings, breaking at 4-3 to serve for the match. At 40-15, Federer had two match points to close out the match but blinked as lightning struck twice.

Djokovic reeled off the last four games and would go on to win his first US Open title as Federer wondered what might have been. The dejected Swiss would say after the match:

"It's awkward having to explain this loss because I feel like I should be doing the other press conference."

Federer would return to the US Open final in 2015 before going down to Djokovic in four sets.

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#4. Rome 2006 Final: Rafael Nadal beats Roger Federer 6-7(0), 7-6(5), 6-4, 2-6, 7-6(5)

Roger Federer (right) squandered match points against Nadal in the Rome final.

Roger Federer and Rafael Nadal combined to provide a match for the ages in the final of the 2006 Rome Masters.

Federer was the undisputed World No. 1 coming into the match, having been the world's top-ranked player for more than two years. However, Nadal was creating his own legacy, especially on the red dirt, and was proving to be the perfect antidote to Federer's picture-perfect free-flowing game.

Having won only one of the pair's five previous meetings, and none on clay, Federer was unafraid to attack the net against the relentless baseliner as he pocketed the opening set. Nadal leveled proceedings in the next, but Federer took the all-important two-sets-to-one lead.

Once again, Nadal refused to go away, forcing a decider where he double-faulted at 5-6 to give Federer two championship points. However, the Swiss hit long and then wide as the match entered a tiebreak.

Leading 5-3, Federer missed a routine midcourt forehand that would have given him three more match points. Nadal pounced and reeled off the next three points to seal the victory. It remains the only match in 40 meetings between the legendary pair that the winner saved match points and won in a deciding set tiebreak.

Nadal said after the five-hour, five-minute clash:

“I was lucky that when he had match points. He made a mistake with two forehands, one which was quite simple for him.”

That would be the closest Federer would come to winning Rome, as he fell short in three other title matches - one of them against Nadal (2013).

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#3. 2017 Australian Open Final - Roger Federer beats Rafael Nadal 6-4, 3-6, 6-1, 3-6, 6-3

Roger Federer (right) beat Nadal in the Australian Open final.

Roger Federer met his good friend and arch-rival Rafael Nadal in a dream title match at the 2017 Australian Open.

Despite both players returning to action after a few months on the sidelines, they booked an unlikely clash in the final where there were ebbs and troughs aplenty to keep fans on the edge of their seats.

Playing his 28th Major final, and first at the Australian Open in seven years, Federer made a bright start by pocketing the opener. However, Nadal fought back to take the second before the Swiss took the pivotal third set. Once again, the Spaniard pegged back Federer to force a decider, where he led 3-1.

This time, it was Federer's turn to flip the script. He reeled off five straight games, including saving two break points while serving for the match, to end his four-and-a-half-year Grand Slam drought and win his 18th Major title.

Federer, who became the first 17th seed to win a Major since Pete Sampras at the 2002 US Open, said:

“I don’t think either of us believed we’d be in the final. I’m happy for you (Nadal). I would have been happy to lose, to be honest. The comeback was as perfect as it was.”

The Swiss would go on to win two of the next four Majors, including his sixth title at the Australian Open, the following year.

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#2. Wimbledon 2019 final: Roger Federer beats Andy Roddick 5-7, 7-6(6), 7-6(5), 3-6, 16-14

Roger Federer (2R) won his 15th Major title at 2009 Wimbledon.

Roger Federer reached his seventh straight Wimbledon final in 2009 but faced a monumental challenge from Andy Roddick. The American threw the kitchen sink at Federer, who responded with the "bathtub", as Roddick would later surmise.

"I threw the kitchen sink at him but he went to the bathroom and got his tub."

He could not have said it better, as Roddick was the better player for large swathes and came within a whisker of a two-set lead. The American took the opener 7-5 but saw four straight set points in the second set tiebreak come and go as Federer fought his way back into the match.

The Swiss then took the third set on a tiebreak, but Roddick wasn't going anywhere. Playing arguably the best tennis of his career, the American rode a lone break to force a decider, where both players were clutch on serve - especially Roddick.

However, serving to stay in the Championship for the 11th consecutive time, Roddick lost serve for the first time in the match - which also drew the contest to a close as Federer became the first male player to win 15 Grand Slam titles.

Federer, who sent down 50 aces - survived 27 from Roddick - to improve to 18-2 against the American. The Swiss would later say about the pivotal second set.

“I thought the second set was obviously key to what came after. Maybe being down two sets to love, the way Andy was serving, would have always been a very difficult situation to be in. Even then down two sets to love it's still possible, but it definitely increased my chances of winning.”

Federer would win two more titles at Wimbledon, while Roddick would retire three years later without adding to his 2003 US Open triumph.

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#1. Wimbledon 2019 final: Novak Djokovic beats Roger Federer 7-6(5), 1-6, 7-6(4), 4-6, 13-12(3)

Roger Federer on Day Thirteen: The Championships - Wimbledon 2019

Roger Federer suffered one of the most agonizing losses of his illustrious career in the 2019 Wimbledon final.

Not for the first time, the Swiss rued squandering match points - on serve - against Novak Djokovic as he went down in one of the best finals in the history of the grasscourt Major.

In a tight first set, Federer squandered a 5-3 lead in the tiebreak as Djokovic drew first blood. However, the Swiss responded in kind to restore parity. Federer then saw break points come and go as Djokovic edged out another tiebreak to take a two-sets-to-one lead. Once again, Federer fought back to force a decider.

After recovering from a break down, Federer served for the match at 8-7 and arrived at 40-15 - two championship points for a record-extending ninth Wimbledon title - but blinked in the most inopportune moment as the Serbian broke back.

To his credit, Federer fought on gamely and squandered a break point at 11-11 before a first-ever Wimbledon fifth ensued. Djokovic reeled off the last four points to win his fifth title at SW 19 as Federer wondered what might have been.

At three minutes shy of five hours, it was the longest Wimbledon final in history as Djokovic became the first player since Robert Falkenburg in 1947 to save championship points in a Wimbledon final.

Federer couldn't have played a better match - winning 14 more points, 40 more winners (94-54), more breaks of serve (7-3), and more first and second serve points won than his opponent. However, Djokovic was clutch where it mattered most - in the three tiebreaks - and of course on the return of serve.

It was his third victory over Federer in a Wimbledon final, having beaten the Swiss in the title matches in 2014 and 2015. It would be the last time Federer would make a Grand Slam final, having come within touching distance of becoming the oldest Major winner in the Open Era and the first to win 21 titles.

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