Holders Peel at Ramsey
Having wrapped up yet another Premier League title, St. George's are halfway on the route to the Grand Slam.
They turn their attention to the Friends Provident International FA Cup and a visit to Division Two side Marown.
There are three all top-flight ties - Old Boys host St. Mary's, Corinthians travel to Rushen and holders Peel go to Ramsey.
Governor's Athletic have reached the last sixteen for the first time and go to Douglas Athletic.
Elsewhere, Douglas & District entertain Ramsey Youth Centre, Colby make the trip to Foxdale and Pulrose welcome Braddan.
Holden 'proud' of FC Isle of Man efforts this season
Rugby: Douglas head to Vale of Lune for play-off challenge
Hockey: IoM Women's Over-45's set for EH Championship semi-final
Football: 2026 Hospital Cup & Junior Cup competitions to get underway
'It's a great opportunity' Island cricketers speak on chance to represent European sides