Chris Lyons dumped his home town club out of the EA Sports cup with a double at Dalymount Park as Bohemians beat Bray Wanderers 4-2 in extra-time to make the quarter-finals.
Holders Drogheda United, Sligo Rovers and Cork City all eased through also. But St. Patrick's Athletic had to work hard to beat First Division bottom side Salthill Devon in extra-time at Drom while both Derry City and Limerick needed penalties to see off Finn Harps and Waterford United respectively to advance to the last eight.
Bray came back from 2-0 down as the sides swapped four goals in a thrilling first half in Phibsboro, but neither side could find a winner in 90 minutes.
Striker Lyons rifled home to put Bohs 3-2 up with the help of a strong deflection in the first minute of extra-time.
Kevin O’Leary then sealed Bohs' passage seven minutes later when turning well in the box to shoot to the net.
Bohs had started positively and were a deserved goal up through Stephen Traynor on six minutes with Lyons adding his first of the night from a penalty seven minutes later.
Bray settled and stormed back into the game to troop off level at the break. They got a goal back on 32 minutes when skipper Danny O’Connor forced the ball just over the line following a Danny Joyce corner.
A sublime passing move resulted in Bray equalising on 39 minutes, Sean Hurley eventually putting over a cross from the left for Ismahil Akinade to score with a well-placed downward header.
Holders Drogheda cruised to a 6-0 win over First Division leaders Longford Town at Hunky Dorys Park.
Dean Gaynor fired Drogheda ahead from a Jason Marks cross on 10 minutes.
Defender Marks then scored twice inside three minutes to put Drogheda well in command by the break, doubling the lead on 26 minutes before finishing off a cross from Gaynor.
Marks then blew the chance of his hat-trick when his 53rd minute penalty was saved by Town keeper Paul Hunt after a foul by Keith Quinn on Peter Hynes.
But Hynes did get a fourth for Drogheda when converting a 59 minutes penalty after he again was hauled down, this time by Willo McDonagh.
Central defender Alan McNally and striker Graham Rusk added fifth and sixth goal on 73 and 77 minutes to complete the rout.
Sligo Rovers also eased through as a brace of goals from Anthony Elding helped them beat Mervue United 4-0 at the Showgrounds.
Elding scored his first from an 18th minute penalty after Mervue midfielder Barry O'Mahony was sent off for handball on the goal line.
Central defender Evan McMillan added a second goal on the hour mark to all but seal the First Division side's fate. Danny Ventre, on 69 minutes, and Elding with his second in the first minute of added time, completed the rout.
St. Patrick's Athletic needed extra-time to beat plucky Salthill Devon 3-2 at Drom.
Enda Curran stunned an albeit under strength St. Pat's to put the First Division's bottom side ahead on 51 minutes.
Saints responded to level on the hour when a Jake Kelly shot took a strong deflection to the net. With 90 minutes failing to separate the side, Brian Geraghty put Devon back in front 11 minutes into extra-time.
But Kelly again levelled for St. Pat's four minutes later before substitute Peter Durrad snatched the winner in the 118th minute.
Striker Rory Patterson scored for Derry City and was then sent off as they needed penalties to beat Finn Harps in Ballybofey after a 1-1 draw.
Patterson put Derry ahead on 17 minutes with a terrific strike from the edge of the area.
But Harps levelled on the stroke of half-time thanks to a fine header by Aaron O'Hagan.
Patterson was then sent off for a second yellow card offence on 75 minutes.
With the rest of the regular 90 minutes and a half an hour of extra-time failing to separate the side, Derry finally prevailed in sudden death penalties 6-5.
Barry Sheedy scored a 90th minute equalise for Limerick to force extra-time against Waterford United at Thomond Park.
The game finished 1-1 in 90 minutes with Stephen Bradley hitting the winning spot kick for the Shannonsiders who advanced 4-2 on penalties after extra-time.
Waterford had taken the lead from a counterattack on the half hour, Aidan McGrath doing well to cross for Vinny Sullivan to head home.
Danny Furlong scored twice against his former club as Cork City eased to a 4-0 win over Wexford Youths at Ferrycarrig Park.
Goals from Ian Turner and Shane Duggan had Cork in control at half-time. Turner fired City ahead from a 30th minute free-kick with Duggan doubling the lead with a spectacular 30-yarder three minutes later.
Furlong got his first on 54 minutes before sealing the win with a second seven minutes later.