It was penalty shoot-out heartache for Derry City for a second time in a matter of days, as St Patrick's Athletic secured a 4-3 victory on penalties, after an entertaining FAI Cup round two encounter ended scoreless.
The Candystripes will feel, just like Thursday night's Europa Conference League defeat, they had the chances to win the clash in normal time.
Derry began the encounter with a good tempo and they had St Pat's on the back foot in the early stages, with Adam O'Reilly and Brandon Kavanagh both going close with long range efforts. A clever pass in from the left by Paul McMullan found Will Patching free inside the box on 32 minutes, but the midfielder's goal-bound strike from 10 yards was bravely turned away by Saints defender John-Alan McGrath.
Minutes later Saints missed a glorious chance as Conor Carty spun away from Cameron McJannet, but the striker's close range attempted lob over City keeper Brian Maher, flew over the bar.
A slick passing move by St Pat's cut open the City back-line but Sam Curtis' low drive from the right hand side the box was turned around the post by Maher's boot. City were forced into a change on the hour mark with Mark Connolly having to replace Shane McEleney, after the ex-Finn Harps man failed to recover from an early injury.
Both manager's made changes to try and win the game in normal time with Michael Duffy and Sadou Diallo coming on for City, while Thomas Lonergan and Jake Mulraney came off the bench for the Saints. A superb cross by Cameron Dummigan on 71 minutes found Ciaran Coll, but the left-back's header was just off target.
Moments later a lovely Brandon Kavanagh cross from the right found Jamie McGonigle and his glancing header was tipped over by Lyness.
Maher had to make a top drawer save on 80 minutes as substitute Mulraney found fellow sub Lonergan, but his powerful header was parried away by the former Republic of Ireland U21 international.
The woodwork came to the Dubliner's rescue on 83 minutes as Patching's stunning free-kick from the edge of the box, which had Lyness beaten, came crashing back off the post. That Patching free-kick was the final chance either side to score in the 90 minutes, meaning Derry had to play extra-time for the second time in just three days.
Derry went close to finally breaking the deadlock on 111 minutes as Michael Duffy's left wing cross found fellow substitute Daniel Mullen, but his goal-bound snap-shot from close range was blocked by Joe Redmond.
City had the early advantage in the shoot-out as Jake Mulraney fired wide, but Duffy side footed wide and Connolly's final penalty came back off the post, to spark wild celebrations amongst the travelling support.
In the other FAI Cup game on Sunday, Wexford went through to the next round following a 1-0 victory over non-league, St Patrick's CY.
Darragh Levingston grabbed the only goal of the game in the 42nd minute at the Ringsend venue to send the First Division side through.
Derry City: Brian Maher, Ronan Boyce (Sadou Diallo 69), Shane McEleney (Mark Connolly 59), Cameron McJannet, Ciaran Coll; Cameron Dummigan (Ben Doherty 78), Adam O'Reilly, Will Patching (Patrick McEleney 105); Brandon Kavanagh, Jamie McGonigle (Daniel Mullen 78), Paul McMullan (Michael Duffy 69).
St Patrick's Athletic: Dean Lyness, Anthony Breslin, Joe Redmond, Jamie Lennon (Ben McCormack 105), Chris Forrester, Jason McCelland (Jake Mulraney 69), Mark Doyle (Kian Leavy 77), Conor Carty, Sam Curtis (Thomas Lonergan 69 - Mason Melia 113), Adam Murphy (Alex Nolan 87), John-Alan McGrath.
Referee: Neil Doyle (Dublin).