After Rinky Hijikata was beaten 6-2 6-2 by 54th-ranked Serbian Miomir Kecmanovic, fellow Sydneysiders James Duckworth and Chris O'Connell were eliminated on Thursday, as was Li Tu.
Hijikata served up the only five double-faults in his 79-minute contest and was broken four times in the second meeting between the two.
World No.76 Hijikata won their first clash in Los Cabos, Mexico earlier in the year.
The reward for Kecmanovic is a second-round encounter with another Aussie in 20th seed Alexei Popyrin, who is competing in his second event since upsetting Novak Djokovic during a breakthrough run to the US Open fourth round.
O'Connell slugged it out for two hours 13 minutes but went down 7-6 (11-9) 7-6 (8-6) to a fit-again Matteo Berrettini.
Back with a bang 💥— ATP Tour (@atptour) Matteo Berrettini defeats O'Connell 7-6(9) 7-6(6) to record his first ATP Masters 1000 win of the season.@SH_RolexMasters | #RolexShanghaiMasters pic.twitter.com/mqUkXFJcDuOctober 3, 2024
Berrettini had an injury-riddled 2023, enduring foot, ankle and abdominal problems, which saw him spiral in the rankings to 125.
Both players lost serve twice but it was the former world No.6 from Italy who moves on to face 12th-seeded Dane Holger Rune in the next round.
Duckworth suffered a 6-4 6-2 defeat to Belgian veteran David Goffin, while qualifier Tu, a 28-year-old from Adelaide, went down 6-1 7-6 (7-4) to American Marcos Giron, with both matches lasting one hour 27 minutes.
Elsewhere, Czech Jakub Mensik and Dutchman Tallon Griekspoor advance in three sets. Spaniard Jaume Munar moved on in two and teenage Chinese wildcard Yi Zhou was trailing 4-2 to Yoshihito Nishioka when the Japanese was forced to retire with a back injury.
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