Dan Evans and Jack Draper booked their place in the quarter-finals of the National Bank Open, while British No. 1 Cam Norrie lost to the world No. 9.
It is only the second time that two British men have reached the quarter-finals at an ATP Masters event – the last time in Cincinnati in 2001 (Tim Henman and Greg Rusedski).
Evans is in his second career ATP 1000 quarter-final after beating 10e seed Taylor Fritz for the second time in two weeks 7-6(5), 1-6, 7-5.
An inspired performance from the Briton saw him come from 3-0 down in the first set, still keeping his nerve to see the decider, after Fritz broke with Evans serving for the match at 5-4. The 32-year-old was particularly effective at net, getting 74% of the points (26/35) when he volleyed in against the young American.
Evans will now play against Tommy Paul in the last eight – the two faced off once in 2018 in Vancouver qualifying where Evans fought in a three-set battle.
Joining him in the quarter-finals at 20 draper – who is in the final stages of the ATP Masters tournament for the first time in his career. Draper progresses after 17 yearse top seed Gael Monfils was forced to retire in the third round with the Briton leading 6-2, 0-2.
His next match will be against world No. 23 Pablo Carreno-Busta. If he and Evans both win, they will face off in an all-British semi-final.
However, it was not to be for Norriewhose strong run of performances ended in a tough 6-3, 6-4 loss to sixth seed Felix Auger-Aliassime.
Neal Skupski and Wesley Koolhof are set to face fellow Brits Lloyd Glasspool and Harri Heliovaara in the quarter-finals. The third seeds continued their excellent form this season – which saw them win five titles – with a 6-3, 6-4 win over Norrie and Alex De Minaur.
Meanwhile, Hamburg champions Glasspool and Heliovaara put in an impressive performance to eliminate experienced duo Simone Bolelli and Fabio Fognini 6-3, 6-4.
Completing the UK roster in the men’s doubles draw is Evans – who is one of the two remaining players in both draws (along with Hubert Hurkacz). Evans and his Australian partner John Peers upset fifth seeds and Wimbledon runners-up Nikola Mektic and Mate Pavic 2-6, 6-3, 14-12 to take on second seeds Marcel Granollers and Horacio Zeballos.
There was, however, a shock loss for top seeds Joe Salisbury and Rajeev Ram, who were beaten by Ariel Behar and Gonzalo Escobar 6-4, 7-6 (3).