ATP roundup: No. 2 seed Ben Shelton falls in Stuttgart

Australian qualifier James Duckworth pulled off a three-set upset of American No. 2 seed Ben Shelton, 7-6 (5), 4-6, 6-3, on Thursday to advance to the quarterfinals of the Boss Open in Stuttgart, Germany.

Shelton fired 21 aces but committed eight double faults along the way. In a close match, Duckworth capitalized on Shelton's second serves, winning 18 of 30 second-return points (60 percent).

Duckworth's next foe will be Italy's Matteo Berrettini, who is playing on a protected ranking. Berrettini took care of Canada's Denis Shapovalov 6-4, 6-4 in 74 minutes on Thursday.

Elsewhere, No. 7 seed Jan-Lennard Struff of Germany defeated France's Arthur Rinderknech 6-4, 7-6 (0), and Brandon Nakashima swept past French lucky loser Richard Gasquet 6-3, 6-4 in 71 minutes.

Libema Open

Top two seeds Alex de Minaur of Australia and Tommy Paul of the U.S. advanced in ‘s-Hertogenbosch, Netherlands.

The top-seeded de Minaur topped Belgian lucky loser Zizou Bergs 7-5, 6-4, while No. 2 seed Paul needed three sets to rally past Australia's Alexei Popyrin 5-7, 6-4, 6-3. Popyrin saved 8 of 11 break points, but Paul hit 10 aces and had fewer unforced errors (11 to Popyrin's 18).

Paul's next foe will be fellow American and seventh seed Sebastian Korda, who beat Italian Luca Nardi 7-5, 7-5. Canadian Milos Raonic will meet de Minaur in the quarterfinals after charging back for a 4-6, 6-2, 7-5 victory over Spaniard Roberto Bautista Agut.

The No. 4 seed in the bracket fell when Australian Aleksandar Vukic beat Russian Karen Khachanov 6-4, 5-7, 7-6 (4). Vukic fired off 14 aces without a single double fault.

--Field Level Media