Novak Djokovic is back in Indian Wells for the first time since 2019. After a first-round bye, his tussle with Aleksandar Vukic heads our list of five matches to watch on Saturday.

1. Novak Djokovic vs Aleksandar Vukic
Head-to-Head: First meeting

Dealing with an elbow injury last season, Vukic considered retiring. But the University of Illinois alum persevered and gets the chance to face the 24-time Grand Slam winner. 

“Yeah, I’ve heard of this guy,” laughed the Aussie after his two-tiebreak win over Shintaro Mochizuki. “For me, he’s the greatest of all time, so I’ll have to see what all the fuss is about.

“This is almost a dream in a way because when you look back on your career, you want to play these matches. Who knows how much he’s got left in him so it’s nice to be able to play him.”

The World No. 69 struggled with more injuries in the last six months (shoulder, adductor), yet 2023 marked his best season. He reached his first ATP final, played three majors for the first time in a campaign and collected a maiden Top 20 win at Toronto in August. There, he also won perhaps the point of the tournament against Gael Monfils after taking a tumble.

Djokovic’s last loss in his opening match at a hard-court regular season event came in Miami in 2018. Yet the 36-year-old hasn’t played since the end of January.

“I think if you want to play him, you probably want to play him now,” said Vukic. “He’s had a big break. I don’t know if that will affect him too much but it’s kind of like you gotta be optimistic otherwise you’ve already lost when you’ve gone out there.”

2. Naomi Osaka vs Liudmila Samsonova
Head-to-Head: First meeting

Osaka won the title here in 2018 as an unseeded player.

The four-time Grand Slam champion reiterated after her 6-3, 6-1 win over Sara Errani in blustery conditions on Thursday that she didn’t mind not having a bye this edition, either, since she is looking for more matches as part of her comeback.

“I think it was an advantage for me to play a first-round match and I’m just really excited to keep going through the tournament,” said Osaka, who gave birth to daughter Shai in July.

Unlike Errani, Samsonova is a power player who finished fifth last season in aces. The 14th seed is no stranger to going deep at WTA 1000 tournaments, making the final in Canada last summer after downing Aryna Sabalenka and Elena Rybakina.

3. Jessica Pegula vs Anna Blinkova
Head-to-Head: Pegula leads 3-0

Pegula contests her second tournament since splitting with longtime coach David Witt, who has since joined Maria Sakkari’s team.

“I just felt like I needed to take some chances,” said Pegula. “I’m 30 – not that being 30 is the end – and I think I just didn’t want to look back and be like ‘Maybe I should have tried someone else, or tried something different.’”

Although a Top 10 regular, Pegula seeks to push on and end her 0-6 skid in Grand Slam quarterfinals. In Indian Wells, Pegula hasn’t advanced past the quarterfinal, either.

Pegula will face Blinkova for the second time in as many weeks, after needing a third set to dispatch the 25-year-old last week in San Diego.

Blinkova, too, upset a resurgent Karolina Pliskova in the first round — two months after defeating Rybakina at the Australian Open in an outing that produced the longest singles tiebreak in Grand Slam history (22-20).

4. Tommy Paul vs Alex Michelsen
Head-to-Head: Paul leads 1-0

Although making his main draw debut in Tennis Paradise this year, Michelsen is no stranger to the Indian Wells Tennis Garden, having won the Easter Bowl as a junior at the venue in 2022. Moving up the tennis ladder, the Orange County native picked up his first Masters 1000-level victory Thursday against Jaume Munar, 6-2, 6-3.

One of four teens inside the Top 100, the 19-year-old also played Paul tough in their lone meeting last month in Delray Beach, losing in a third-set tiebreak in three hours. But in main-draw play in Indian Wells, Paul has never lost to an unseeded player.

5. Holger Rune vs Milos Raonic
Head-to-Head: First meeting

Update 3/9/24 - Milos Raonic has withdrawn from the 2024 BNP Paribas Open, Holger Rune advances to Round 3

Milos Raonic’s blockbuster first-round match with Rafael Nadal didn’t materialize as the Spaniard was forced to pull out, still not ready to compete.

In came a near namesake, ‘Nagal,’ as in lucky loser Sumit Nagal. Despite a rain delay and a visit from the trainer for a lower leg issue, the injury-hit veteran prevailed 6-3, 6-3.

In his first Indian Wells match since 2019, Raonic’s big serve didn’t get broken. He’ll likely need it to be working against the seventh-ranked Dane. The Canadian bids for a first Top 10 win away from home soil since 2020 in Cincinnati.