Britain’s Cameron Norrie earned a notable scalp by beating Bulgarian ninth seed Grigor Dimitrov to reach the Miami Open third round for the first time in his career.
Norrie won 7-5 7-5 against Dimitrov – who reached last month’s Australian Open quarter-finals – to claim a second win over a top-20 opponent this season.
“It is a massive win for me and I will take a lot out of it,” said Norrie, 25.
Dan Evans plays later on Friday, while Katie Boulter lost in the WTA event.
British number one Evans, seeded 19th, faces American Frances Tiafoe after 23:00 GMT.
He will be hoping to join Norrie in the last 32 after the world number 56 outplayed and outlasted Dimitrov to continue his fine start to the 2021 season.
On the significance of beating Dimitrov, Norrie told Amazon Prime: “It is huge. He is really good on the hard courts and had a good start to the year.
“It was an absolute battle. He came out fast and set the tone for the match, then I was able to be solid towards the end of the first and toughed him out in the second.”
Boulter, 24, faded after a fast start as she lost in straight sets to Belgian 16th seed Elise Mertens in the second round.
Now 319th in the world and playing with a injury-protected ranking, Boulter broke for a 3-0 lead and had a chance for the double break at 4-0 before Mertens found her level.
Mertens saw off the break point to hold for 3-1 and seized control – forcing errors as she troubled Boulter with variety of play – winning 6-4 6-1.
Japan’s world number two Naomi Osaka – the reigning Australian Open and US Open champion – earned her 22nd match win in a row by beating Australia’s Ajla Tomljanovic.
After receiving a first-round bye, Osaka started the tournament by fighting back from a break down to win 7-6 (7-3) 6-4.
Osaka stopped her opponent serving out the first set at 5-4 before going on to win the tie-break, then pounced for the only break of the second set for a 5-4 lead which she converted into victory.