Alexander Zverev’s early-season struggles continued on Friday as the No. 1 seed lost a dramatic three-setter to Cristian Garin in the quarterfinals of the BMW Open in Munich, 6-4, 5-7, 7-5.

With the loss, Zverev will lose his No. 3 ranking on Monday to Roger Federer.

Zverev, who was the two-time defending champion in Munich, and was looking for his 10th consecutive win at the 250-level event, seemed on the verge of a miracle comeback victory. After fighting off three match points with Garin serving for the match at 5-4 in the second set, Zverev eventually held two match points of his own at 5-4 in the third set. But Garin had one last burst, winning 12 of the last 13 points of the match from double-match point down to squeak out the two-hour, 11-minute stunner.

Garin is now through to his third ATP semifinal of the year, having reached the final of Sao Paulo in March—falling to Guido Pella—and winning the first ATP title of his career in Houston in April.

The 22-year-old Chilean’s win over the 22-year-old Zverev was the first Top 10 win of his career. Awaiting Garin in the semifinals will be 2018 French Open semifinalist Marco Cecchinato, who also saved a match point in his 1-6, 7-5, 7-5 quarterfinal win over Marton Fucsovics earlier in the day.

Meanwhile, Zverev had come into Munich feeling optimistic.

“Obviously I didn’t play my best the past few weeks, but I feel good on the court. I’m happy on the court, and this is the most important thing,” he told “I feel like my game is pretty much back on the practice courts in the way I hit the ball, but I just have to show it in the matches. I think I’ll have a few very tough matches and if I win them, I think I’m in good shape. We’ll see how it goes.”

The next two weeks could be critical for Zverev. The tour heads to Madrid and Rome, where he did phenomenally well last year, winning the title in Madrid and reaching the final in Rome—falling to Rafael Nadal in a tough three-setter. He’ll be defending almost a third of his ranking points over the next two weeks—1,600 out of 5,565, which will be his total ranking points on Monday.

Zverev, who is already projected to drop from No. 3 to No. 4, will have to fight to hang onto that No. 4 ranking over the next two weeks. Dominic Thiem, who’s currently ranked No. 5, will be 480 points behind the 22-year-old on Monday but only has 610 points to defend in Madrid and Rome—last year he made the Madrid final, falling to Zverev, but lost his opening match in Rome to Fabio Fognini.

The French Open seeds are made after Rome, so there’s an extra incentive for a Top 4 ranking.

Top-seeded Zverev falls in Munich, will lose No. 3 ranking to Federer

Top-seeded Zverev falls in Munich, will lose No. 3 ranking to Federer