Andy Glover ensured the FA Cup holders made a winning start to their defence of the trophy.
He scored the only goal of the game as St Mary’s overcame battling Gymns 1-0 at Tromode in Saturday’s preliminary round.
Union Mills also had to battle before seeing off second division opposition.
They ran out 4-2 home winners over Ayre United, courtesy of goals from Matty Cain (two), Chris Kelly and Ronan McDonald.
Phil Quayle netted a brace for the Tangerines with all the goals coming in the first half.
Second half goals from Gary Christian and Stuart Morris – who also missed a penalty – fired Marown to a 2-0 success over a spirited Braddan.
Ronaldsway also put up a spirited showing before going down 4-2 at home to Douglas Royal.
Stuart Foley, Paddy Dempsey, Ryan Kelly and Paul Whitley grabbed the goals with Dave Walker and Luke Callister replying for the Rockets, who led 1-0 at the break.