Novak Djokovic\u2019s latest attempt at winning a 100th ATP Tour title has ended at the first hurdle.<\/p>\n
The fifth seed was stunned in straight sets in his opening match at the Monte Carlo Masters, falling 6-3, 6-4 to world No 32 Alejandro Tabilo<\/a>.<\/p>\n Victory for Tabilo extends a significant run in Monte Carlo for the Chilean, who battled past another former champion \u2013 Stan Wawrinka \u2013 in the first round.<\/p>\n And, it also maintains his perfect record against Djokovic.<\/a><\/p>\n Tabilo has played the former world No 1 twice and has won both times, making him one of just three men to play Djokovic multiple times \u2013 and never taste defeat.<\/p>\n Former world No 19 Tabilo has faced Djokovic on clay the past two years \u2013 and has beaten the Serbian on both occasions.<\/p>\n The Chilean dominated Djokovic when they met at the Italian Open last May, breezing past the six-time Rome champion with a 6-2, 6-3 third-round victory over the then-world No 1.<\/p>\n Despite that, Tabilo was a significant underdog heading into this clash; he had a disappointing 3-9 record for 2025 before this match, while Djokovic came in off reaching the Miami Open final.<\/p>\n However, in a match not too dissimilar from their Rome encounter almost 12 months ago, Tabilo made a flat Djokovic pay with another impressive straight-sets victory.<\/p>\n Perhaps the least surprising name on this list is Safin, a former world No 1 and two-time Grand Slam champion at the peak of his powers.<\/p>\n The Russian won the second of his two Grand Slam titles at the Australian Open in 2005 \u2013 and beat Djokovic on his way to glory.<\/p>\n Having come through qualifying to make his Grand Slam main draw debut, a 17-year-old Djokovic was drawn against Safin in round one \u2013 and was thrashed 6-0, 6-2, 6-1.<\/p>\n Three years later, the two met in the second round of Wimbledon \u2013 and this time the Serbian was the favourite to win.<\/p>\n Djokovic was the third seed and the reigning Australian Open champion, while Safin had fallen down the rankings.<\/p>\n However, the Russian channelled past glories with a scintillating display, stunning the world No 3 6-4, 7-6(3), 6-2, ultimately going on to reach the last four.<\/p>\n Carlos Alcaraz reacts to shaky Monte Carlo start\u00a0as he\u00a0reveals \u2018most important adjustment\u2019\u00a0<\/a><\/p>\n Carlos Alcaraz handed huge rankings opportunity after Alexander Zverev\u2019s demise<\/a><\/p>\n In one of the craziest stats in tennis history, Vesely \u2013 a man who has never been ranked inside the top 30 of the ATP Rankings \u2013 has a perfect 2-0 record against the 24-time Grand Slam champion.<\/p>\n Much like with Tabilo, one of Vesely\u2019s two wins over Djokovic came in the second round of Monte Carlo.<\/p>\n Nine years ago, Djokovic came into the 2016 Monte Carlo Masters as the reigning champion and as a dominant world No 1 \u2013 only to be stunned 6-4, 2-6, 6-4 by the Czech in his opener.<\/p>\n Six years later, the two met for a second time, and once again it was Vesely who proved to be a surprise victor.<\/p>\n The former world No 35 defeated Djokovic 6-4, 7-6(4) in the quarter-final of the Dubai Tennis Championships, the most recent meeting between the two.<\/p>\n Djokovic and Vesely were set to face off in the second round of the 2016 US Open, though the Czech was forced to withdraw pre-match.<\/p>\n Read Next<\/strong>:\u00a0How Monte Carlo has become Novak Djokovic\u2019s weakest Masters 1000 event<\/a><\/p>\n The post The 3 men to hold a 2-0 record over Novak Djokovic: Alejandro Tabilo joins exclusive club<\/a> appeared first on Tennis365<\/a>.<\/p>","protected":false},"excerpt":{"rendered":" Novak Djokovic\u2019s latest attempt at winning a 100th ATP Tour title has ended at the first hurdle. The fifth seed was stunned in straight sets in his opening match at the Monte Carlo Masters, falling 6-3, 6-4 to world No 32 Alejandro Tabilo. Victory for Tabilo extends a significant run in Monte Carlo for the […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-280","post","type-post","status-publish","format-standard","hentry","category-articles"],"_links":{"self":[{"href":"https:\/\/tennisring.com\/index.php?rest_route=\/wp\/v2\/posts\/280","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/tennisring.com\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/tennisring.com\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/tennisring.com\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/tennisring.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=280"}],"version-history":[{"count":0,"href":"https:\/\/tennisring.com\/index.php?rest_route=\/wp\/v2\/posts\/280\/revisions"}],"wp:attachment":[{"href":"https:\/\/tennisring.com\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=280"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/tennisring.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=280"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/tennisring.com\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=280"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}Alejandro Tabilo (2-0)<\/h4>\n
Marat Safin (2-0)<\/h4>\n
Monte Carlo Masters News<\/h2>\n
Jiri Vesely (2-0)<\/h4>\n