The Warilla Wanderers will make the long trip up to Picton to kick off round two of the Bert Bampton Cup.
Football South Coast announced the draw for round two and three of the Cup on Tuesday. University and Berkeley will meet in a catch-up game on July 1, before the second round is held on the weekend of July 4 and 5.
Round two will feature District League teams. Oak Flats will also tackle Unanderra Hearts, Helensburgh faces Fernhill while the winner of Uni and Berkeley will meet Thirroul.
Warilla coach Nathan Peglar said he expected a tough challenge from Picton.
"Playing at home up there, they've got the conditions and ground suited to their style," he said.
"It will be hard to travel up there and get the win... but the boys are raring to go to get back into it."
Illawarra Premier League sides will then join the Cup on July 11 and 12.
Illawarra Premier League sides will then join the Cup competition on July 11 and 12.
Woonona faces South Coast United, Corrimal will take on Coniston, Cringila meets Tarrawanna, Wollongong Olympic meet Bellambi and Port Kembla hosts Albion Park White Eagles.
Reigning Cup premier Bulli will meet the winner of Oak Flas and Unanderra, Uni/Berkeley/Thirroul will host Wollongong United while the winner of Picton v Warilla will face the winner of Helensburgh/Fernhill.
The Bert Bampton Cup's return will mark three-and-a-half months since players last took to the field.
A handful of Cup games were played on March 14 before football went into shutdown due to COVID-19.
Warilla advanced to round two with a 4-3 win over Balgownie, Picton beat Kiama 3-0 and Thirroul sealed a 2-1 win over Shell Cove FC.
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