In a career lined with records and milestones, Roger Federer is within touching distance of one more: 100 singles titles. As the 37-year-old begins his 20th year on the tennis tour—itself an achievement, given how many of those years he has spent at the top and being the hunted—it’s a number waiting to be rounded. Then, there’s Jimmy Connors.

With 109 titles, Connors holds the record in the Open Era—beginning 1968, when the artificial wall dividing professionals and amateurs came down—for the maximum number of singles titles. He’s held it since 1989, when he won the last of his tournaments, ironically at the same age as Federer is now.

In an interview last year to The New York Times, Federer said that breaking Connors’s record of 109 titles was not his “ultimate goal". If it really was, he added, he would skip more top-tier events, which have tougher draws, and play more second- and third-rung tournaments. This distinction that Federer makes is a point of distinction between the bucketful of titles of Federer and Connors.

In top-flight men’s tennis, there are three rungs of tournaments. At the first level, there are principally the four grand slams and the nine masters events, which top players are rarely selective about. Below this comes the ATP 500 and ATP 250 events, where the fields are relatively weaker.

As many as 53 of Federer’s 99 titles have come in the top-tier tournaments. His other two illustrious contemporaries, Rafael Nadal and Novak Djokovic, are better on this count. While they are on 80 and 72 total titles, respectively, both have a return of 51 titles from top-tier events.

This is a point of contrast with Connors, only 28 of whose titles came from the big events.

It’s partly a construct of the tennis tour being more fragmented in the 1970s and 1980s, when Connors played. For example, leading European players did not cross over to the US regularly and instead played similar lower-level events in Europe. Of his 109 titles, the American with the fiery temper and a fierce game won 75 of his 109 titles in the US.

While a rider on the tiered nature of tournaments might be in place, no such thing can be said about Connors’s longevity. Or that of Federer’s. Both players won their first title at the age of 20 years, and both have 18 years separating their first title and their last/latest title.

However, there are differences. By the young standards of tennis, Federer was a relatively late bloomer. He turned professional in 1998, at the age of 17 years.

However, he won his first tournament in 2001.

Among the set of top three title winners and his two chasing contemporaries, Federer had the slowest start on the title count. Till the age of 22 years, he trailed all of them in titles, with 11 titles, against 32 for Connors and 31 for Nadal. However, once he found his groove and a touch of invincibility, Federer went on a run, accumulating 42 titles between the age of 23 and 26.

What’s more remarkable is what Federer has done in his 30s. In his 30s, Connors became recognized more for scripting stirring comebacks in grand slam five-setters, but not so much for titles. He won 13 titles in the nine years he played into his thirties. Federer, by comparison, has won 29 titles in his 30s (chart 2).

While Federer has run through a significant part of the arc of his 30s, Nadal and Djokovic are just about beginning that stretch where the tendency of the body is to disregard the mind and the heart. Ask Andy Murray, who is still appended to this troika but who announced this week that this will be his last year because of a hip ravaged by the years. If he does retire, he would do so at the age of 31 with 45 titles.

In their own ways, Nadal and Djokovic are also feeling the physical strain of playing top-flight tennis, which only amplifies what Federer is doing today.

Each player in our set of five shows a preference for certain surfaces.

Of these five, Federer’s title portfolio is the most diversified across three surfaces. In other words, he does the best job of maximizing his strengths (grass and hard courts), while squeezing out something from his least-favoured surface (clay).

Playing on a limited schedule, Federer won four tournaments last year and also briefly held the top ranking.

He won tournament number 99 in October 2018. Number 100 could be a matter of time and it would still just be a statistic.

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