Australia’s Alexei Popyrin has been knocked out of the Rotterdam ATP tournament at the first round stage by Karen Khachanov in a tight three-set match.

The Australian world No.66 was beaten 7-6 (4), 1-6, 6-7 (8) in just over three-and a-half-hours. He had chances to defeat Khachanov, who is ranked 38 places higher, but could not take them.

Popyrin won the first set on the tie-break in 62 minutes. But he double-faulted early in the second on break point before losing the set in a swift 23 minutes.

Popyrin came back strongly in the third set, forcing a break-point match-point at 5-4, but could not make it count.

He was then twice a break-point up in the third-set tie-break, leading 5-3 and serving at one stage, but could not maintain the advantage.

Popyrin served twice as many aces (10) as his opponent but was only able to break the Russian once.

His defeat leaves Alex de Minaur as the only Australian left in the draw.