2019 Milestones: Djokovic, Nadal, Federer, Serena chasing history

Court Report: Roger Federer, Rafael Nadal, and Novak Djokovic look ahead to 2019

From top players writing themselves deeper into the history books to first-time breakthroughs, the 2018 tennis season was historic—but 2019 could be just as historic, if not more.

Here are some milestones to watch for in 2019 (and some could happen as early as January).

Djokovic Goes for Grand Slam Title No. 15: With one more major victory, Novak Djokovic will pass his childhood idol, Pete Sampras, to become standalone third place on the men’s list for most Grand Slam titles in tennis history. The two of them are currently tied at 14, trailing only Roger Federer (20) and Rafael Nadal (17). The Serb will likely be the favorite to win the Australian Open in January.

Nadal Goes for French Open Title No. 12: Nadal won his 11th French Open title this year, which tied him with Margaret Court for most career titles at a single Grand Slam event for a man or woman in tennis history (Court won 11 Australian Opens). If he wins one more title at Roland Garros, he’ll become the first tennis player ever—male or female - to win the same Grand Slam event 12 times.

Federer Chases ATP Title No. 100: He was two wins away twice at the end of the 2018 season, falling in back-to-back semifinals in his last two tournaments of the year in Paris (to Djokovic) and the ATP Finals (to Alexander Zverev). But Federer will have plenty of opportunities to win his 100th career ATP title in 2019, a milestone only one man has ever crossed (Jimmy Connors won 109 career titles).

Serena Tries to Tie (or Break) the All-Time Grand Slam Record: Like Federer, Serena Williams came close to reaching her most imminent milestone twice in 2018, reaching the finals of both Wimbledon and the US Open. But if she wins her 24th Grand Slam title in 2019, she’ll tie Court’s all-time record for most career Grand Slam titles for a man or woman (and a 25th would break it).

Serena Tries to Become the First 100 Million Dollar Woman: As of now, there are three tennis players in existence who have crossed $100 million in career prize money, and they’re all men: Djokovic, Federer and Nadal. Serena’s the only other player anywhere near that milestone with $88,233,301, and she’s made that difference in a season before (she earned $12,385,572 in 2013).

The Depth in the Women’s Game Could Reach a Historic Level: 2017 and 2018 marked the first two-season period in 80 years where eight different women won the eight majors. But if four different women win the four majors in 2019—and none of them won any in 2017 and 2018—it’ll be the first time in tennis history that 12 different women have won the 12 majors in a three-season period.

The ’90s-Born Men Chase Their First Major: Seven ‘90s-born women have already won majors, but no ‘90s-born men have won any yet—in fact, there aren’t even any active Grand Slam champions on the men’s side under the age of 30 right now. But two ‘90s-born players have won the ATP Finals (Zverev and Grigor Dimitrov) and four have won Masters 1000 titles (Zverev, Dimitrov, Jack Sock and Karen Khachanov) so it might just be a matter of time before a breakthrough.

Naomi Osaka Tries to Become the Highest-Ranked Japanese Player Ever: Currently ranked No. 5, Osaka went as high as No. 4 shortly after her dream run at the US Open, which tied her with former No. 4s Kimiko Date and Kei Nishikori as the highest-ranked Japanese players ever. Other than her Indian Wells title, she has very little to defend until the US Open, so Top 3 is within reach.

Federer & Serena Try to Become the Oldest Grand Slam Champions in the Open Era: As of now, the oldest player to win a Grand Slam title in the Open Era—male or female—is Ken Rosewall, who won the 1972 Australian Open at the age of 37 years and 62 days. Federer and Serena are both an older age 37 right now, so if either of them win any of the four majors in 2019, they’ll raise the bar.

Will any of these milestones happen? What other big things do you think could happen in 2019?