Lorenzo Musetti gave Novak Djokovic an early clay-court blow as he reached the Monte-Carlo Quarter-Finals with a 4-6 7-5 6-4 victory.
The Italian produced the best victory of his career after a scrappy rain-delayed contest saw him beat the world number one.
Djokovic was seen with a protective cover over his arm and will have a lot to ponder as he plays in Bosnia next week.
Musetti will now face compatriot Jannik Sinner in Friday’s Quarter-Finals.
Despite an impressive start to the match from both players, the contest was a scrappy one as neither play adapted successfully to the conditions.
Djokovic broke in imperious fashion in the fourth game to take a 3-1 lead before the Italian responded immediately with a break of his own.
Musetti constantly took his aggressive tennis to Djokovic with the top seed displaying some stubborn defence as he looked to force some erratic errors from the Serb.
In the end Djokovic’s defence prevailed as he took a 4-2 lead and threatened the double break lead in the eighth game.
Despite showing resilience to not only prevent the double break but to break back, Musetti produced too many unforced errors as Djokovic’s consistency prevailed, claiming the opening set 6-4. 4
The Italian’s service jitters continued in the second set as he was broken on four occasions as he was passive mentally and tactically.
However Djokovic’s arm continued to bother him with this match turning into a scrappy affair.
The world number one couldn’t produce enough power or consistency to neutralise Musetti’s hard hitting as Djokovic was broken on five occasions.
Musetti fired up the crowd as this match was going to a deciding set in slow conditions.
Early in the third set, there was a small rain delay which allowed Djokovic to gain tactical clarity as he looked to improve his level.
Although both players improved the quality of their serving after the restart it was Musetti who managed to take more risks, breaking in the seventh game for a 4-3 lead.
After a tense final game, Musetti overcame Djokovic’s resilient attack as he sealed the biggest win of his career.
In his post-match interview Musetti described what the victory meant, “It is an emotional win because it was a really long match,” Musetti told the ATP website.
“Three-hour match and suspended by rain. It was not easy conditions because it was a little bit windy and cold. Not like we used to play in the recent days. I am really proud of myself and I can see on the screen. I am struggling not to cry because it is a dream for me.”
Djokovic will ponder his future and will look to improve ahead of next week’s 250 event in Bosnia.
As for Musetti he will have to remain fresh and recover for the challenge of Jannik Sinner as a place in the last four awaits.