The first day of qualifying matches for the ATP World Tour’s main draw saw the top two seeds winning in straight sets, but included a surprising early exit by American Tim Smyczek.

Smyczek’s string of six consecutive main draw appearances in Delray Beach was snapped when Darian King of Barbados upset the American 6-3, 5-7, 6-4 in the day’s opening match on Court 1.

Bjorn Fratangelo, the No. 1 seed in the singles qualifying draw, held off fellow American Mitchell Krueger 7-6 (4), 7-6 (3) to advance to Sunday’s final day of the qualifying matches that will fill out the main draw.

Also advancing was No. 2 seed Cameron Norrie, the No. 3-ranked Brit who ousted fellow countryman Liam Broady 6-3, 6-1.

American brothers Boris and Stefan Kozlov from nearby Pembroke Pines – competing in the same ATP-level draw for the first time – each lost their qualifying matches to Alexander Bublik and Ramkumar Ramanathan, respectively.

The other winners in the qualies on Saturday were Aussie John-Patrick Smith, Canadian Peter Polansky, and Croatian Franko Skugor. A Polansky win Sunday would put three Canadians in the Delray Beach Open main draw. The top two Canadians—Milos Raonic and Denis Shapovalov—are already playing in a Tuesday afternoon “Canada Day.”

Sunday’s final four qualifying matches will begin at 11 a.m.