Francisco Cerundolo upset Alexander Zverev 6-3 6-4 after 90 minutes to reach the fourth ATP Masters 1000 quarter final of his career.
Cerundolo saved both break points he faced and won 79% of his first-serve points.
Cerundolo becomes the first Argentine player to reach the quarter final in Madrid since Juan Martin Del Potro advanced to the last eight in 2012.
Cerundolo saved two break points at deuce in a 10-minute first game. The first set went on serve until the eighth game when Cerundolo earned a break at 15 to take a 5-3 lead. The Argentine player served out the first set at love after 44 minutes.
Cerundolo broke serve in the third game of second set to take a 2-1 lead. Zverev saved a double break point at 2-4 down. Cerundolo held on his service games and served out the win on his second match point in the 10th game.
Cerundolo is aiming to reach his second Masters 1000 semifinal when he takes on Taylor Fritz, who beat Hubert Hurkacz 7-6 (7-4) 6-4.
Fritz is the ninth US player to reach ten quarter finals at Masters 1000 level. Fritz won the tie-break of the first set 7-4 with two mini-breaks before earning the first break of the match in the first game of the second set. Hurkacz saved three match points as he was serving to stay in the match, but Fritz served out the win on his fourth match point to reach the quarter final in Madrid for the first time in his career. The US player has advanced to a quarter final in a Masters 1000 tournament for the ninth time in his career and for the third time on clay.