Fresh off overcoming veteran Stanislas Wawrinka, Flavio Cobolli is the undoubted underdog against record four-time Shanghai Masters champion Novak Djokovic when the pair face off in Tuesday’s third-round match.

The Italian is seeking a major scalp after eliminating Wawrinka but must play high-level tennis to beat a player who recently secured his 35th victory at this event.

Match preview

© Imago

Although Cobolli was backed to record success over Wawrinka in three sets, Monday’s closely fought battle could have gone either way.

The world No. 30 withstood a staggering 17 access off his Swiss opponent’s racquet to notch a 6-7(6), 7-6(4), 6-3 win over the 39-year-old and set up a round-three battle with Djokovic.

The fact that the sole service break came in the third set underscores the efficient serving from both players, with opportunities to inflict damage few and far between.

Such top-level serving will be required to shock Djokovic, as Cobolli aims to build on securing an 18th deciding-set success of the season on Monday to record his 34th victory in 2024.

© Imago

His Serbian opponent is no newcomer to this stage, having claimed a record four titles in Shanghai and now bidding for a 100th Tour-level victory on his return to the event after a five-year absence.

He was given a fright in his tournament opener against Alex Michelsen on Saturday, needing two tiebreaks and saving two set points in the second before notching a 7-6(3), 7-6(9) success against the young American.

Djokovic found himself 4-1 down in the opening set before losing a 4-1 advantage in the second set in a high-quality battle that saw both players hit more winners (34, 30) to unforced errors (23, 19).

Given his minimal competitive action since a shock US Open third-round exit to Alexei Popyrin, Cobolli will aim to exploit any rustiness from the Serbian’s side of the court in Tuesday’s match-up.

Having had a winless title run at Masters 1000 events this year, the 37-year-old is bidding for his first and 41st overall in the penultimate ATP 1000 tournament of 2024, thus increasing the importance of beating the young Italian.

Tournament so far

Flavio Cobolli:

First round: Bye
Second round: vs. Stanislas Wawrinka 6-7[6] 7-6[4] 6-3

Novak Djokovic:

First round: Bye
Second round: vs. Alex Michelsen 7-6[3], 7-6[9]

Head To Head

Tuesday’s match-up will be the first between both players, with the 22-year-old Cobolli seeking an upset against the sport’s greatest player.

Despite an underwhelming year by his lofty standards, Djokovic’s 33-8 record betters his Italian opponent’s 34-25 heading into their first ATP Tour encounter in Shanghai.