Novak Djokovic has been the Prince Of Paris in recent years, winning 15 of his past 16 matches and taking the title in his past two appearances in 2019 and 2021. But on Thursday at the Rolex Paris Masters the Serb runs into the only player he’s fallen to during that streak: Karen Khachanov.

The 38-time ATP Masters 1000 champion holds a 7-1 Head2Head advantage over his rival, but a straight-sets defeat in the 2018 final in Bercy, where Khachanov claimed his lone Masters 1000 trophy, surely still gives Djokovic some indigestion.

The record holder of 373 weeks as No. 1 in the Pepperstone ATP Rankings is aiming for his fourth victory over Khachanov this season (Dubai, Belgrade, Astana). He is also chasing his fifth title of the year after triumphs at Rome, Wimbledon, Tel Aviv and Astana, the latter two coming in consecutive weeks. The indoor hard-court event in France presents a new challenge, even for the six-time champion.

“The conditions are different,” Djokovic said following his opening match against Maxime Cressy. “From last year, it’s quicker. The balls are fast and they go through the court. It makes it more challenging to break serve.”

Khachanov, World No. 19 in the Pepperstone ATP Rankings, will rely on his heavy first delivery and firepower from the baseline to try his hand at another upset in the French capital in the fourth match on Court Central.

Earlier on Thursday, World No. 1 Carlos Alcaraz will look to back up his strong start in Paris as he faces 2017 Nitto ATP Finals champion Grigor Dimitrov for the first time.

“First round in every tournament is never easy,” Alcaraz said following his opening match. “You have to be really focused, you have to try to get good rhythm, good feeling in the first round. I’m really happy with the performance, the level that I played, and I’m looking forward to getting better in the next round.”

The 19-year-old Spaniard is aiming for his third ATP Masters 1000 crown (Miami & Madrid 2022), which would add to his season-leading five Tour-level titles. He is also looking to tighten his grip on the converted year-end No. 1 Pepperstone ATP Ranking, which will be presented at the Nitto ATP Finals in Turin.

Holger Rune, 19, has reached at least the final in each of his past three tournaments, including in Stockholm, where he collected the title. After the Dane spoiled Hubert Hurkacz’s hopes of returning to the Nitto ATP Finals, the 19-year-old looks to earn back-to-back wins against Top-10 players when he meets Andrey Rublev, whose qualification for Turin was confirmed Wednesday.

Casper Ruud, who still has an outside shot to finish the year No. 1, kicks off Thursday’s card with a first-time meeting against talented Italian Lorenzo Musetti, who next week will spearhead the eight-man field at the 21-and-under Intesa Sanpaolo Next Gen ATP Finals in Milan.

Norway’s World No. 4, a two-time Grand Slam finalist this year, is looking to regain form ahead of his second appearance at the Nitto ATP Finals, where last year he made the semi-finals. Although just two wins shy of his 50th match win on the year, the 23-year-old came into Paris on a three-match losing streak.

.@CasperRuud98 is known for his forehand, and tonight vs Gasquet it was in full flow

FH Shot Quality context 👇
Tour avg. 7.2
Ruud 52-week avg. 8.5 (one of the best on tour)
Ruud vs Gasquet 9.3 🔥#TennisInsights | @RolexPMasters | #RolexParisMasters pic.twitter.com/GRxJQtMVxO

— Tennis Insights (@tennis_insights) November 1, 2022

French World No. 64 Corentin Moutet will return to Court Central less than 16 hours after his early-morning win over Cameron Norrie to battle fifth seed Stefanos Tsitsipas for a place in the quarter-finals. Moutet, 23, closed out a third-set tie-break win over Norrie at 3.04 a.m. Thursday morning.

Tsitsipas, who boasts a 58-21 record on the season, is chasing his second Masters 1000 title of the year (Monte Carlo). He also has an outside shot of pushing for year-end No. 1 honours if Carlos Alcaraz doesn’t have a deep run in Paris and at the Nitto ATP Finals.