ISSA/Digicel Manning Cup on Monday, October 8, 2018, with defending champions Jamaica College hosting Kingston Technical.

Kingston Technical took the lead in the first half and made their presence felt at Old Hope Road, as they silenced the home support taking the one nil lead. However, the fervets showed their championship mentality and equalised minutes after going behind.
The first half ended even at one apiece.

The second half was entirely not what the defending champions expect as they were held by Kingston Technical deep into the game. As the clock ticked and the final result seemed a draw, up stepped the goalkeeper as Kingston Technical won a freekick about 28 yards out. As the crowd touted and jeered him as he approached the ball, with eyes only for goal, the custodian marked his spot before kicking the ball, and it was a beautiful freekick that left his opposite number helpless and grasping at thin air. The fans stood in shock while the Kingston Technical fans ran towards their goal scoring hero.

Jamaica College had now tasted first-round defeat for the first time in six years as their unbeaten record for the season comes to an abrupt end. Fulltime result Jamaica College 1-2 Kingston Technical High.