At the PHC Stadium, the PHC Zebras advanced into the final four of the competition following their 2 - 1 win over the St. George's Colts. The PHC Zebras got on the board first when Jaavaid Warren-Smith followed up a shot that the St. George's Colts goalkeeper Misheal Paynter failed to hang on to and scored from close range. The St. George's Colts were awarded a penalty in the 33rd minute, but David Signor's shot was saved, however the referee's assistant signaled that the goalkeeper was off his line, the spot kick was retaken and scored by Allan Douglas Jr.
The teams went to the break with the score tied at 1 -1. In the 59th minute the PHC Zebras went back in front when Cecoy Robinson scored, his goal proved to be the winner and advance the PHC Zebras into the FA Challenge Cup Semi-Final draw.
X-Road’s 1 Dandy Town Hornets 2
At the Garrison Field, the Dandy Town Hornets advanced to the Semi-Finals with a 2 - 1 come from behind win over X-Road’s. Tyquann Perinchief gave X-Road’s the lead in the 23rd minute only to have Angelo Simmons equalize for the Dandy Town Hornets in the 34th minute. Damon Ming would score for the Dandy Town Hornets in the 41st minute and his goal proved to be the winner as neither team could find the back of the net for the remainder of the match.
North Village Rams 3 Devonshire Cougars 0
At the Bernard Park the North Village Rams defeated the Devonshire Cougars 3 - 0 to advance. The North Village Rams went in front in the 14th minute when Lashun Dill found the back of the net, seven minutes later Demetre Daniels scored to make it 2 - 0. In the 54 minute the North Village Rams were awarded a penalty kick that Shayne Hollis put away.
