Novak Djokovic, the fourth seed and reigning Shanghai Masters finalist, is set to face unseeded Marin Cilic in a much-anticipated second-round match. Djokovic received a bye in the first round due to his top seed ranking, while Cilic advanced after a straight-sets upset victory over qualifier Nikoloz Basilashvili.
For Djokovic, this season has been largely defined by his pursuit of a record 25th Grand Slam title. Although he hasn’t captured this milestone yet, he has demonstrated remarkable consistency, reaching the semifinals in each of the four major tournaments this year. This included a retirement due to a left leg muscle tear against Alexander Zverev at the Australian Open, before succumbing to Jannik Sinner at both Roland Garros and Wimbledon, and facing defeat by Carlos Alcaraz at the US Open. Despite these setbacks, Djokovic celebrated his 100th career title in Geneva and made a commendable run to the finals in Miami, where he faced an unexpected loss to Jakub Mensik. Throughout this season, Djokovic has showcased his prowess on the court with an impressive record of 345 aces, winning 76% of his first-serve points, and converting 42% of break points against his opponents.
On the other hand, Cilic’s journey in 2025 has been marked by resilience following his recovery from knee surgeries. After undergoing operations in early 2023 and mid-2024, Cilic made a slow return to the circuit, winning the 2024 Hangzhou Open along the way. Even though he struggled initially, he has gradually rebuilt his form by claiming Challenger titles in Girona and Nottingham II and reaching the finals in Challenger Madrid. Cilic’s notable performance this season was his run to the quarterfinals in Dubai.
The head-to-head record between Djokovic and Cilic is heavily favored towards Djokovic, who holds a commanding 19-2 lead in their rivalry. Their meetings date back 17 years, with Djokovic winning the first 13 encounters before Cilic finally prevailed in 2016 in Paris. Cilic momentarily tasted victory again at the 2018 London finals, but Djokovic quickly regained dominance, winning their subsequent six matchups.
Considering their contrasting seasons and Djokovic’s strong historical performance against Cilic, the Serbian player is viewed as the favorite heading into this clash. Analysts expect Djokovic’s relentless pursuit of that elusive grand slam title will fuel his performance against a tenacious but still-recovering Cilic. With both players showing their determination, this match at the Shanghai Masters promises to deliver an exciting encounter.
Betting odds reflect Djokovic’s status as the clear favorite at -1200, while Cilic stands at +710, underscoring Djokovic’s consistent performance and past successes in this matchup. As anticipation builds for the match, fans are ready to witness whether Djokovic can continue his dominance or if Cilic can carve out a breakthrough to challenge the reigning champion.