The ABN AMRO World Tennis Tournament continued with eight singles matches, five to conclude the first round and three to start the second round as well as three doubles matches.
Top seed Daniil Medvedev, third seed Alexander Zverev and fifth seed Roberto Bautista Agut were eliminated while fourth seed Andrey Rublev and sixth seed David Goffin advanced.
Medvedev, Zverev, Bautista Agut all sent packing
Medvedev was upset by Dusan Lajovic as the Serb fired off 15 winners in a 7-6 (4), 6-4 victory. It was the Russian who led by an early break only to watch Lajovic rally and break in the sixth game before prevailing in a tiebreak that ended with a double fault by Medvedev.
The Serb held from 15-40 trailing 1-2 in the second set and would go on to secure another break after Medvedev once again double-faulted to give Lajovic a 5-4 lead and he would serve out the match for his fifth career Top 10 victory.
"I think I was very focused the whole match and not influenced by his good serves and shots", Lajovic said in his post-match interview. "I knew if I stayed in the match, i'd get my opportunities and change the rhythm."
Zverev was taken out by Alexander Bublik 7-5, 6-3 in just 77 minutes. The German broke in the very first game of the match before the Kazakh rallied to level at 4-4 and broke again for a 6-5 lead behind powerful forehands and he closed the set out a game later.
Again, Zverev claimed the early advantage, this time holding a 3-1 lead in the second set before world number 43 Bublik won the final five games of the match to record the biggest win of his career.
"Beating Sascha is great", he said after the match. "There were ups and downs for both of us during the match, I got a bit lucky and I was perhaps more consistent. I'm just enjoying playing matches right now."
Bautista Agut was the last of the top seeds to fall as he was knocked out by countryman Alejandro Davidovich Fokina 6-2, 7-6 (3). The 51st-ranked Spaniard converted four of his eight break point opportunities to advance to the second round in 84 minutes.
Rublev, Goffin move on
The headline match of the day was the second-round clash between Rublev and Murray with the fourth-seeded Russian coming out on top 7-5, 6-2 to improve his record in 2021 to 10-1.
After a tight opening set with nothing between them, Rublev struck first when Murray committed back-to-back double faults to go ahead 6-5 and the Russian saved two break points to eventually close out the set.
The second set was one-sided as Rublev went on the offensive, pushing Murray back off of the baseline as he struck his 14th forehand winner of the match to close out the victory.
"The first set was really good. The level was really great", the Russian said in his on-court interview. "He had a couple of chances, a couple of break points. I was a bit lucky in the first set and as soon as I won the first set, I felt more confident.
"I started to feel better. Andy went down a bit mentally, I started to play even better and he slowed down a bit."
Goffin won the final eight games of his first-round encounter with Jan-Lennard Struff, sweeping past the German 6-4, 6-0 in 62 minutes for his sixth straight win after capturing the title in Montpellier last week.
"It was a good match with an early break", the Belgian stated. "I returned really well and I was aggressive after returning serve. I started with a lot of confidence in the second set as I am playing and moving well."
Nishikori, Khachanov, Paul round out singles winners
Tommy Paul advanced in exactly two hours as he knocked off Lorenzo Sonego 6-4, 7-6 (6) in their first-round match, the American saving a set point at 7-6 in the second set tiebreaker.
Kei Nishikori battled past Alex de Minaur 6-3, 2-6, 7-5, breaking the Australian's serve four times and earning his second Top 30 victory of the week.
"I am happy to be in the quarterfinals at this tough tournament:, he said, "I just need to keep going and be ready for the next match."
Karen Khachanov closed out play with a comfortable 6-2, 6-2 win over British qualifier Cameron Norrie after just 75 minutes of action to improve his record to 7-2 on the year.
Top seeds eliminated in doubles
The upsets weren't reserved for just singles as the top doubles team in the world, Juan Sebastian Cabal and Robert Farah were knocked out in the first round by Henri Kontinen and Edouard Roger-Vasselin 4-6, 6-3, 11-9 with the Finnish-French duo saving two match points.
Third seeds Wesley Koolhof and Lukasz Kubot were also sent packing by the French team of Jeremy Chardy and Fabrice Martin 6-4, 6-3 in their second-round clash. Chardy and Martin saved all three break points they faced.
Stefanos Tsitsipas teamed up with his brother Petros to rout the Belgian tandem of Sander Gille and Joran Vliegen 6-2, 6-3, who won in Singapore, to reach the second round.
Following the match, Stefanos announced that for every doubles win he gets with his brother, he will donate 3,000 euros to Mazi gia to Paidi (Together For Children), whose mission is, “to provide immediate and effective support to children, families, and individuals with disabilities who are in need”.