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Chris O'Connell will face Andy Murray, and James Duckworth is a win away from meeting Daniil Medvedev, as the grasscourt season picks up.
With the claycourt swing having concluded at Roland Garros the grasscourt build-up to Wimbledon has intensified with two Australians facing major tests.
In Stuttgart, Germany, Chris O'Connell has been rewarded for battling through qualifying with an attractive first round match against three-time grand slam champion Andy Murray.
That match is on Tuesday along with Nick Kyrgios's opener against Czech Jiri Lehecka.
On Monday veteran Feliciano Lopez was beaten 6-4 6-1 by Benjamin Bonzi and sixth-seed Lorenzo Sonego overcame Benoit Paire 7-5, 6-2.
In 's-Hertogenbosch, in the Netherlands, James Duckworth has a second round meeting with world No.2 Daniil Medvedev if he beats an as-yet undetermined qualifier on Tuesday.
Aussie No.1 Alex de Minaur has a first round bye. He will meet Adrian Mannarino or a qualifier in the second round.