Drogheda United had two players sent off, along with head coach Tim Clancy, as they ultimately paid the penalty to bow out of the FAI Cup to Derry City in a cliffhanger first round tie at Head in the Game Park.
The game finished 1-1 after extra-time with the Candystripes prevailing in the necessary shoutout, 4-2.
Drogheda edged the first half taking the lead deep in stoppage time.
Killian Phillips controlled Massey’s long throw to drill a ball across the visitors’ goal for Dinny Corcoran to slide in to finish at the back post.
Central defender Massey was then sent off for deliberate handball eight minutes into the second half to concede a penalty.
But there was a reprieve for the home side as Junior Ogedi-Uzokwe’s spot kick hit the post Drogheda right-back James Brown was then dismissed in the 80th minute for a second yellow card offence with Clancy also sent to the stand by referee Paul McLaughlin.
With Drogs looking like they might somehow hold out with nine men, Derry were awarded a second penalty five minutes into added time when Luke Heeney tripped Junior. Danny Lafferty stepped up to slot home from 12 yards to force extra-time.
Evan McLaughlin came within inches of winning it for Derry when striking a post with a free kick before the game went to penalties.
Derry goalkeeper Nathan Gartside proved the Derry hero in the shoutout with saves from James Clarke and Phillips before McLaughlin scored from the spot to put Derry into Tuesday’s second round draw.
The goal frame and frantic defending meant Premier Division Finn Harps needed extra-time to see off Fairview Rangers in Limerick, the FAI Junior Cup holders finally succumbing 3-0 at Fairgreen.
Sean Boyd finally put the Premier Division side in front in the fifth minute of extra-time. An own-goal added to that before Barry McNamee scored a third in added time at the end of extra-time.
Longford Town had five different scorers as they eased through with a 5-0 defeat of Dublin non-league side Bangor GG FC at Bishopsgate.
Dean Williams put Town in front on 16 minutes with a poacher's finish.
But it was 65 minutes before the Premier Division’s bottom side doubled their lead from a Dylan Grimes penalty.
Midfielder Darragh Nugent blasted home the goal of the game five minutes later before Callum Warfield and Aaron O’Driscoll added late headed goals to give the Midlanders their first win in 21 games.