Guernsey side Vale Rec came from behind to beat Portuguese Club 2-1 in their historic Le Riche Cup first-round tie.
Vale became the first Guernsey team to enter Jersey's showpiece knockout competition.
Portuguese took the lead through Ryan Poingdestre but two second-half goals from Sean Mills sent Vale through.
There were no major shocks in Saturday's first-round ties and only one Championship side remains in the draw for the quarter-finals.
Jersey Premiership champions St Paul's thumped St Brelade 5-1, while a Dominic Glennon hat-trick helped First Tower United beat Beeches OB by six goals to two.
Jersey Scottish were also comfortable winners, overcoming St John 6-0 with six different scorers.
In the other games, Jersey Wanderers beat struggling Rozel Rovers 4-1, Magpies were beaten 3-0 by Grouville and St Ouen lost 1-0 to St Peter.
In the all-Championship tie, St Martin/SCF beat Sporting Academics 4-1.
The quarter-finals are scheduled for 21 January.