The Irish League side got off to a bright start, with Timmy Adamson testing Gerard Doherty's goal in the fourth minute. Chris Morrow should have put Crusaders ahead in the 10th minute, but saw his free kick come back out off the post. Derry were slow to get into the match, and when they did, never really troubled Sean O'Neill's goal in the opening half. They won a few corners near the end of the first 45 minutes, and David McDaid had a decent chance, but shot wide.
Crusaders regained the momentum in the second half, with route one football paying off. A quick counter attack saw Chris Morrow force Doherty into a save, and when the rebound fell to Declan Cadell, the Hatchetmen really should have taken the lead. However, Cadell drove it over, and Derry remained in the game. David Rainey hit the post when through on goal, but was incorrectly ruled off for offside. Another long ball immediately after won a corner, with Adamson hitting the crossbar.
Doherty pulled off another great save, tipping Rainey's long-range effort over with a quarter of an hour remaining as Crusaders pushed for a winner. 36-year-old Rainey was Crues' key man, delivering excellent through balls and looking a constant threat in attack.
Derry City finally broke the deadlock with 10 minutes remaining; substitute Owen Morrison sent in a cross for Patrick McEleney, who controlled the ball excellently in the box, to set up Rory Patterson to squeeze the ball past O'Neill for his sixth goal of the tournament. The Northern Ireland international forward had been quiet for most of the game, but when his chance came, he took it well to give Derry the lead against the run of play.
With five minutes to go, Crusaders equalised in controversial circumstances. Rainey clattered into Doherty as a free kick was sent into the box. With Doherty on the ground clutching his head, captain Colin Coates headed into an empty net to set up a lively finish. Rainey looked to have won it minutes after, but his shot rippled the side netting, with half the ground thinking it had gone in.
Rory Patterson claimed for a penalty with a minute left, after going up with O'Neill for a high ball. Referee Ray Crangle was quick to award a free out and showed Patterson a yellow card for his protests. Moments later, Simon Madden was on the receiving end of a late challenge from Stephen McBride, which saw the Crusaders defender receive his second yellow card to leave Crues with 10 men for extra time.
The first real chance of the half fell to Declan Cadell, but Ryan McBride got across to make an excellent slide tackle to put it out for a corner. Doherty tried to claim the corner, but couldn't hold it, allowing Coates to poke the ball in for his fourth goal of the tournament.
Derry restored parity from the spot in the 12th minute of extra time. The referee pointed to the spot when Paul Leeman blocked the ball with his arm, and Rory Patterson scored his second of the evening. O'Neill got his hand down to the penalty, but the ball trickled in at the right post to make it 2-2.
Doherty pulled off another splendid save shortly after, keeping Coates out to stop the Crusaders captain getting a hat trick. Neither side created much in the second half of extra time, with many of the players looking jaded after over 100 minutes of football.
In the shootout, Patterson, Higgins, Molloy, and Patrick McEleney all scored for Derry, while Coates, Morrow, Snoddy, Dallas, found the net for Crusaders, but Morrison put his spot kick wide, as did Ciaran Gargan for Crusaders. O'Neill saved Dermot McCaffrey's penalty to see Gareth McKeown hit the winner for Crusaders.