Barry Holland was the loneliest man at Solitude last night as his spot-kick miss sent last year's beaten finalists crashing out of the CIS Cup.
The Reds had battled back from two goals down to take the tie to extra-time and when David McAlinden bagged his second of the evening the Reds looked set for a place in the last four only for Cullen Feeney to grab a dramatic late leveller for Newry to send the tie to penalties.
The first chance of the game fell to Ronan Scannell but after setting himself in the area he sent his right-footed effort wide.
Brother Chris drew a fine save from Robert Robinson before City took the lead on 16 minutes. A corner from the left was flicked on at the near post and Stephen Garrett was on hand to poke the ball over the line.
The Reds threatened to pull themselves level and went close through a Kieran O'Connor volley before John Martin hit the post with a header.
Newry captain Richard Clarke brought a smart save from Reds' goalkeeper John Connolly on 34 minutes but just 60 seconds later grabbed the visitors' second with a neat finish.
Garrett came close to adding a third right on half-time but was denied by a magnificent last gasp challenge from Declan O'Hara.
Cliftonville continued to huff and puff after the interval but rarely looked like getting back into things until the 68th minute when John Martin nipped round Robinson to net a timely first goal for the club.
That was that until two minutes from time when referee Trevor Moutray spotted a hand ball in the Newry area and suddenly the home side had a lifeline which McAlinden wasn't about to pass up as he smashed home from the penalty spot.
He repeated the trick six minutes into extra-time after Roman Scannell had been felled in the area by Robinson. The raiding full-back did his best to keep his footing but as soon as he hit the floor the whistle sounded and McAlinden lashed home his second of the night.
That looked set to send Cliftonville through but out of nowhere Newry grabbed a third of their own in injury-time when Cullen Feeney headed home.
Then came that penalty shoot-out and after Friars, Clarke, Lee Feeney, Kevin Keegan, Niall Hudson and Tony Smith had all netted for Newry, Barry Holland was asked to do what team-mate Barry Johnston, Chris Scannell, McAlinden, Ryan Catney and O'Connor had done before him but he sent his spot kick high over the bar.
CLIFTONVILLE: Connolly, Smyth, R Scannell, Johnston, O'Hara, McAlinden, Martin, O'Connor, C Scannell, Catney, G McMullan. Substitutes: O'Neill, Gowdy, C McMullan, B Holland, Devine.
NEWRY CITY: Robinson, Hudson, C Feeney, McLaughlin, E Friars, Clarke, McDonnell, Ferguson, Anderson, Garrett, King. Substitutes: Keegan, Smith, Curran, L Feeney, Donegan.
Referee: Trevor Moutray (Belfast)