Federers’ first grand slam triumph came at Wimbledon in 2003, and it was also the first time he had such a large television audience. When the score was tied at two in the first set tiebreaker, Federer showed off all of his skill in one point, including a half-volley from the baseline, wide-angled groundstrokes, and a beautiful forehand down the line.

2) Andre Agassi won the 2005 US Open Final image

Federer began the match by unleashing an absurdly strong forehand from well behind the baseline against the sentimental audience favorite Agassi, who was perhaps playing against the crowd for the first time in his career (around the 28 second mark in the video above). The veteran American appeared incredulous. Later, Agassi would recall the encounter, saying, “There was no safe spot to throw a ball on the court when I faced Roger Federer in the 2005 US Open final.” Rogers had outstanding serve, return, moves, and net game; his versatility was so strong that he may have had five separate strengths that were better than anyone else on the Tour.

3) 2009 FRENCH OPEN SEMI-FINAL vs. Juan Martin Del Ponte

After suffering a crushing loss to Rafael Nadal in the 2009 Australian Open final, Federer was eager to win the French Open in order to complete his career grand slam. When Robin Sderling upset Nadal in the fourth round, Federer realized this might be his best chance to win in Paris. But the 6’7″ Del Potro and his tenacious ground game presented him with a significant physical challenge. But Federer managed to escape with a five-set victory by using a variety of strategies. Federer managed to chase down a forehand in the second game of the match, curving the ball down the line to win. The Swiss master then proceeded to thrash unexpected finalist Sderling in the championship match to claim his lone French Open victory.

4) Andy Roddick vs. 2009 Wimbledon Final image

After taking part in what many consider to be the greatest match ever played at SW19, losing to Nadal in five thrilling sets, Federer returned to the Wimbledon final and engaged in yet another epic a year later. Roddick won the opening set and then dominated the tiebreaker with a commanding 6-2 advantage. Roddick appeared to be in rather good control of the point when he served for a seemingly insurmountable two-set lead before he blasted a forehand at Federer’s feet. However, Federer won the tiebreak with a carefree half-volley backhand winner (at about the 4:45 point in the video above). He would triumph in an amazing fifth set 16-14.

5) NOVAK DJOKOVIC

2010 US OPEN SEMI-FINAL

Several opportunities Roger Federer missed are included on this list because of their importance. It seemed as though it would actually happen in 2010, with New York supporters drooling at the prospect of a Federer-Nadal final (unfortunately, Gotham never got to see the two square battle). Serving with a 15-40 deficit, Djokovic flubbed two opening serves. However, Federer became tense on both occasions, allowing Djokovic to strike (disclaimer: these two points are included as one).

6) 2011 FRENCH OPEN SEMI-FINAL VS. DJOKOVICI

Federer was in his first career slump when the 2011 French Open rolled around; he had gone four straight major slams without winning a match. Nadal, who had just completed a three-grand slam season in 2010, and Djokovic, who had started the year brilliantly by winning 41 straight matches, including the Australian Open a few months earlier, were the two players everyone was talking about going into the tournament. A clearly motivated Federer defeated Djokovic in four sets, pulling off a major upset. Around the two-minute mark in the video above, Federer manages to pull off a flipped backhand down-the-line passing shot that stuns Djokovic and helps secure the victory in the last set of his victory after both greats have traded brilliant smashes from all over the court. When the match was over, he showed everyone how much the win meant to him by waving his finger in the air. Although Nadal crushed Federer in the championship match, it didn’t diminish the significance of this victory.

7) V DJOKOVIC

2011 US OPEN SEMI-FINAL

Surprisingly, Federer found himself up two match points in the same round in New York just a year after surrendering two match points to his adversary in the semi-final. It was on his serve this time. And to save the opening match point, Djokovic came up with an absurd return this time. Then, on the second match point, Federer botched a straightforward forehand into the back of the net, clearly spooked by what Djokovic had just accomplished on the first match point. In a rare display of obvious annoyance following the match, Federer remarked that Djokovic didn’t seem to have much faith in succeeding. It’s incredibly disheartening to lose to someone like that because you get the impression that he was already mentally unbalanced. Just makes the fortunate shot at the last end, and you’re off.

8) 2017 AUSTRALIAN OPEN FINAL VS. NADALImg

Federer entered the Australian Open with minimal enthusiasm because his career had already been formally declared finished after he struggled with medical problems and subpar results in the majors. The same can be said about Nadal, who had just emerged from what was perhaps his worst stretch of his career. But in Melbourne, the two put on a performance. Nadal entered the match with an undefeated record against Federer, having discovered the secret to defeating him (high balls to the backhand side). Federer’s backhand didn’t sag on this particular day. But as demonstrated by this play in the third set, which gave Federer a break point, it was his all-powerful forehand that delivered him the victory. Federer managed to hit a half-volley down the line with terrifying power, giving him an advantage (45 second mark above). The third act of Federer’s spectacular career would begin after he recovered from a break down in the fifth set to win the title.

9) TOMAS BERDYCH

vs. 2017 MIAMI OPEN QUARTER-FINAL

Okay, so this wasn’t a particularly significant match or competition for Federer (although he did win it). However, it must be included because the shot—a mid-court, high-in-the-air drop shot that absolutely duped Berdych—is so exceptional.

10) DJOKOVICI vs. 2019 Wimbledon Final image

It may seem unfair to conclude on a negative one for Federer, but the defeat disguised the startling realization that, despite being just weeks away from turning 38, an old age in tennis, Federer was still just one grand slam victory away. It must have hurt that it all happened against Djokovic. The match was once again in Federer’s hands (around the 40-second mark above), but this time, he opted for conservative serves that Djokovic handled with what appeared to be ease. I don’t know what I feel right now, a despondent Federer said after it was finished. It simply seems like such a huge chance was lost that I can’t believe it.

That may be the case, but given how frequently Federer came so near to perfection, mistakes like this stick out in his career.