Keno Proctor netted three times for defending champions St Clair Coaching School to stop lower division club Calder Hall FC 3-0 in the Tobago Football Association FA Cup last Thursday.
On the same day, First Division outfit Youth Stars United dispatched Premier Division club and 2009 winners Stokely Vale FC via a 5-4 scoreline on penalty kicks.
The game was goalless at the end of regulation time, before Youth Stars prevailed in a tight contest from the penalty spot.
Youth Stars also booted out another top division team from this year's competition, beating Georgia United 3-0 at the Dwight Yorke Stadium (DYS) in Bacolet on Monday.
On the same night, Stokely Vale were 2-1 winners over First Division side Signal Hill United.
In the meeting between Coaching School and Calder Hall, Vernon Wilson netted the fourth item for Coaching School, who stayed on track to repeat their double title success last season.
Champs Coaching School whipped Hill United 7-0 in their previous game at the DYS, while Calder Hall stopped their counterparts from the First Division Carnbee/Mt Pleasant 2-1 at Plymouth.
On Tuesday, Sidey's FC beat their neighbours and 2005, 2007 and 2008 champions Roxborough Lakers 3-0 in the first affair at Goodwood.
Pavel Warrick netted a brace and Rondell Johnson scored the other item for Sidey's.
In the opening encounter, Charlotteville Unifiers advanced to the next stage with a 3-1 success over Federal Northside.
Garth Woodley notched a double, while Kevin McKenna had the other effort for Unifiers. Juma George netted for Northside.