Dundalk secured the first of what they hope will be a treble but they were taken all the way by Derry City.
In a fantastic encounter in front of a packed Brandywell, the sides couldn’t be separated until penalties, with Chris Shields firing home the winning penalty to secure a 6-5 win.
The Candy Stripes had to play with ten men for over an hour of the encounter, after Grant Gillespie was sent-off.
Ally Gilchrist's penalty rattled back off the crossbar in the sudden death shoot-out, leaving Shields to calmly slot home the winning spot-kick.
Derry got off to the perfect start when they broke the deadlock on two minutes after a goalkeeping error by Aaron McCarey.
The net-minder failed to hold onto Junior Ogedi-Uzokwe’s shot from just inside the box and the alert David Parkhouse was on hand tap home the loose ball from virtually on the goal-line.
Dundalk would have equalised on 11 minutes but for a top drawer stop by Peter Cherrie.
Jamie McGrath’s run and cross from the right hand side of the box found an in-rushing Michael Duffy whose powerful header was somehow tipped over by the Derry keeper.
Dundalk deservedly levelled things on 38 minutes in stunning fashion as Michael Duffy cut in from the left and his sublime curling effort from the edge of the box sailed into Cherrie’s top left hand corner.
Derry, who brought on Darren McCauley for the injury Gerardo Bruna at the break, regained the lead on 50 minutes in somewhat fortunate circumstances as Junior Ogedi-Uzokwe broke in from the right before seeing his goal-bound strike take a deflection off Sean Hoare on it’s way past a flat-footed McCarey.
The Brandywell men were rightfully reduced to ten men as Grant Gillespie, who was booked minutes before, was given a second yellow card followed by a red after stupidly bringing down Jamie McGrath.
Cherrie was called into action on 64 minutes as Chris Shields’ stinging 25 yard drive was tipped over by the City keeper.
Five minutes later the sides were level for a second time, with that man Duffy at the heart of things, cutting in from the left and seeing his low drive fumbled by Cherrie and Sean Gannon was on hand to turn home the loose ball.
In the closing minutes it was the ten men who were pushing for a winner, but Ciaron Harkin’s tame effort was saved by McCarey.
Right at the death, Patrick McEleney went on a trade mark run before his goal bound strike from the edge of the box, was blocked by Ciaran Coll.
Duffy had a great chance to give Dundalk the lead for the first time on 100 minutes as Pat Hoban feed the winger, he cut inside past McDonagh and Eoin Toal, but his well hit drive from 10 yards was kept out by Cherrie.
Derry had a glorious chance to take the lead for a third time as substitute Michael McCrudden got in behind the Dundalk defence 108 minutes, but his left footed shot from just inside the box was straight at McCarey.
Derry City: Cherrie, McDonagh, Toal, Gilchrist, Coll; Bruna (McCauley HT Delap 118), Gillespie, McNamee; Harkin, Parkhouse (Malone 77), Ogedi-Uzokwe (McCrudden 101).
Dundalk: McCarey, Gannon, Hoare, Cleary, Massey; Shields, McEleney (Jarvis 102), McGrath (G Kelly 86); Duffy, Hoban, D Kelly (Benson 66).
Referee: Robert Hennessy (Dublin).