James Duckworth and Aleksandar Vukic have each pulled of one of the biggest wins of their careers to reach ATP 250 quarter-finals on the European grasscourt circuit.
Duckworth beat world No.14 Ben Shelton in Stuttgart while Vukic defeated former top-10 player Karen Khachanov, now ranked 22, in s'-Hertogenbosch.
It was Duckworth's third career win over a top-20 player and his best since defeating then-world No.13 David Goffin in Miami in 2021. A few months later that year he defeated Jannik Sinner, then No,15, now the No.1, in Toronto.
Khachanov was Vukic's second highest-ranked victim having previously beaten Borna Coric, then ranked 15th, in Toronto last August.
The results are a boost for both ahead of Wimbledon. Vukic has a place in the main draw while Duckworth will have to go through qualifying unless he gets a place as an alternate. He was fifth on the list but Rafael Nadal has already dropped out of the event.
Also into the last eight in the Netherlands is Alex de Minaur. After finding himself 2-5 down against Belgium's Zizou Bergs he won five successive games to take the first set before easing through the second for a 7-5 6-4 win. De Minaur, the top seed, now meets Milos Raonic.
But Alexei Popyrin is out despite winning the first set against second-seeded Tommy Paul. The American recovered to win 5-7 6-4 6-3 and will now face compatriot Sebastian Korda.
Vukic's win took two days and was a test of nerve. The 28-year-old Sydneysider prevailed in a final set tiebreak having twice failed to serve out at 5-4.
Having taken the first set on Wednesday he was left to stew overnight after play was suspended due to darkness after Khachanov won four successive games to win the second set.
Resuming on Thursday Vukic again broke early to take a 5-3 third set lead, but Khachanov again broke back as Vukic served for the match at 5-4.
However, in the tiebreak a thumping forehand by Vukic set up a 6-3 lead and three match points. On the second the fourth-seeded Russian went long after another strong Vukic forehand.
That clinched a 6-4 5-7 7-6 (7-4) victory in two hours, 39 minutes.
Vukic, currently ranked 87 after a difficult few months on clay, now faces defending champion, sixth-seed and local hope Tallon Griekspoor in the quarter-final. The pair have never met.
In Germany Duckworth, 101st in the world, won 7-6 (7-5) 4-6 6-3 in two hours four minutes. It was his first win over a top-100 opponent since early February
When the American wrapped up the second set in 35 minutes to level it looked as if Duckworth's day would be done, but the match went with serve until Duckworth, aided by a pair of double-faults, broke in the eighth game to take a 5-3 lead. He then served out, winning with his second match point.
The 32-year-old will now play former Wimbledon finalist Matteo Berrettini who beat Dennis Shapovalov 6-4 6-4.
