German lucky loser Jan Lennard Struff battled past Stefanos Tsitsipas 7-6 (7-5) 5-7 6-3 to reach his first Masters 1000 semifinals at the Madrid Mutua Open.
Struff set up a semifinal clash against another lucky loser Alsan Karatsev, who beat Zhang Zhizhen Zhang. They will face for the second time in the tournament after they met in the qualifying round.
Struff becomes the third lucky-loser in history to reach the semifinals of a Masters 1000 tournament following Thomas Johansson in Toronto 2004 and Lucas Pouille in Rome 2016.
The German was called back into the draw as a lucky loser and beat Lorenzo Sonego, Ben Shelton and Stefanos Tsitsipas to advance to his first Masters 1000 semifinal after reaching the quarter final at the Monte-Carlo Rolex Masters last month.
Tsitsipas earned earned two break points at 2-2, but he was not able to convert them. The next three games went to deuce, but both players held on serve to set up a tie-break. Tsitsipas went up a 4-1 lead with an early mini-break on the second point, but Struff earned two mini-breaks to win seven of the next ten points to take the tie-break 7-5.
Tsitsipas earned the only break point in the first game of the second set. Both players went on serve in the next game. Tsitsipas took a 5-4 lead with an ace. Tsitsipas earned three break points at 5-5 in Struff’s next service game. Struff saved them, but Tsitsipas earned his first break after the German made a double fault.
Tsitsipas earned two break points at 1-1 in the third set. Struff held serve before breaking serve in the next game on his first break point in the match. Struff saved a break point in the seventh game to hold serve for 5-2 and served out the win on his second match point at 5-3.
“It feels amazing. It was a very hard battle. I knew before I needed to perform at my best. I an very happy that I played so well today. The crowd was amazing. It was an unbelievable atmosphere and I am really that I won”, said Struff.