Think back to the dominant force that was Novak Djokovic at the 2013 Monte Carlo Open. After twice falling in the Monte Carlo final to Rafael Nadal (in 2009 and 2012), Novak Djokovic finally broke through that year, ending Nadal’s seemingly unbreakable streak of 46 consecutive wins at the prestigious event. Two years later, he won his second title at the tournament, becoming the first man to achieve a clean sweep of the season’s initial three ATP Masters 1000 tournaments. Since then, his trophy cabinet has swelled by 47 more, including an Olympic gold in Paris just last year, bringing his career total to 99. So, as he stepped onto the Monte Carlo clay this year, the anticipation for his 100th title was palpable. Yet, tennis can be brutally unpredictable.

Alejandro Tabilo delivered a stunning first-round upset on Wednesday. Chilean southpaw stunned the tennis world, delivering a clinical 6-3, 6-4 victory over the Serbian GOAT Novak Djoković. The 27-year-old was in sublime form, capitalizing on a sluggish performance from the 24-time GS champion, who racked up 29 unforced errors in a surprisingly flat start to his clay-court campaign.

This unexpected defeat against the Chilean not only stalled Djoker’s centurion quest but also linked the Chilean star to a particular record held by none other than Rafael Nadal – a connection Djokovic might prefer to forget as he looks ahead to Madrid. What is this surprising parallel?

Right after Novak Djokovic’s surprising loss in Monte Carlo, the official X page of “Tennis.com” highlighted an intriguing feat achieved by Chile’s Alejandro Tabilo, quoting, “DID YOU KNOW❓With a 6-2 6-3 win in Rome last May and a 6-3 6-4 win in Monte Carlo today, 🇨🇱 Alejandro Tabilo is just the fourth man EVER to win his first two meetings with Djokovic without losing a set. 💥💥 The other three? Nadal, [Marat] Safin and [Nick] Kyrgios.” 

Nadal won his first meeting with Djokovic in the 2006 Roland Garros QFs, 6-4, 6-4, retired (after Djokovic had to stop because of a back injury), then beat him 6-2, 7-5 in the 2007 Indian Wells final. 

Safin’s the only one to do it in two Grand Slam meetings, defeating him in the first round of the Australian Open in 2005, 6-0, 6-2, 6-1, then in the second round of Wimbledon in 2008, 6-4, 7-6 (3), 6-2.

Kyrgios is the only one to do it in the same year, 2017, and at back-to-back events too, beating him in the QFs of Acapulco, 7-6 (9), 7-5, then in the 4th round of Indian Wells, 6-4, 7-6 (3). 

Moreover, Tabilo now also joins the rare company as the ninth player ever to secure a 2-0 head-to-head against Djokovic, after Roger Federer, Rafael Nadal, Marat Safin, Guillermo Coria, Fernando Verdasco, Nick Kyrgios, Olivier Rochus, and Jiri Vesely. Along with that, Tabilo is the only one in the group to win his first two meetings with Djokovic in a completed match and without going to a tie-break. 

While the Chilean now gears up to face Grigor Dimitrov in the R16, Novak Djokovic, a semi-finalist in Monte Carlo a year ago, opened up about the disappointment of delivering such a below-par performance, one that further delays his long-awaited 100th career title.

Novak Djokovic shares his thoughts after “horrible” Monte Carlo run

Novak Djokovic’s journey to a historic 100th career title has been a dramatic chase. Since capturing Olympic gold on the red clay of Paris last year, the Serbian legend has scoured the globe for that elusive milestone, battling through the US Open, Shanghai Masters, Australian Open, and a string of hard-court tournaments. A finalist finish in Miami sparked renewed hope, especially with Monte Carlo, familiar clay under his feet, on the horizon. But tennis, like life, writes its own script, isn’t it?

On a breezy Wednesday afternoon, Djokovic was once again undone by Chile’s Alejandro Tabilo. Right after the loss, Novak said, “It was actually more like the worst day. Look, I was hoping it was not going to happen, but it was quite a high probability I’m going to play this way. I don’t know. Just horrible. Horrible feeling to play this way, and just sorry for all the people that have to witness this. I expected myself at least to have put a decent performance. Not like this. It was horrible. I did not have high expectations, really. I knew I’m gonna have a tough opponent and I knew I’m gonna probably play pretty bad. But this bad, I didn’t expect.”

Looking ahead, the Serb now shifts his focus to the Madrid Open later this month, where he’ll have Andy Murray by his side for support. And despite the setback in Monte Carlo, Djokovic has made it clear that his clay-court campaign is centered on one ultimate goal: triumphing at Roland Garros. However, after this stumble, can the 24-time Grand Slam champion bounce back and reignite his fire at the Madrid Open?