O'Reilly piles on the misery for Hoops
Shamrock Rovers 0 Longford Town 1
Daniel O'Reilly hit a late winner to dump Shamrock Rovers out of the EA Sports Cup and ramp up the pressure on Stephen Bradley.
Having laboured throughout before a paltry crowd of just 304, Rovers failed to clear an 89th-minute corner, giving O'Reilly the chance to drill a low shot into the corner of Tomer Chencinski's net.
Longford are now away to Cobh Ramblers in an all-First Division quarter-final.
With nine changes to the team that started last Friday's 1-1 draw with Limerick, and teenagers Eric Abulu and Brandon Kavanagh making their debuts, Rovers struggled to impose themselves on opponents who passed the ball well.
Town midfielder Jamie Hollywood skied a shot over the top before the midlanders weren't far off taking the lead in the game's first real chance on 22 minutes when Sam Verdon was narrowly off target after good play by ex-Hoop Darren Meenan and Karl Chambers.
Three minutes later, Town's good attitude resulted in another clear opening. Tristan Noack-Hofmann got forward on the left to pick out Dean Byrne with a low cross. The striker turned cleverly on the edge of the area before curling a left-foot shot just past Chencinski's right-hand post.
Rovers didn't conjure an opportunity until the 43rd minute. David McAllister's cross from the right was nodded down by Gary Shaw into the path of Kavanagh, whose crisp left-foot volley was inches wide of a post.
Rovers were better on the resumption, pinning Longford back. But they struggled to create much. Ethan Boyle did have the ball in the Longford net with a header from fellow substitute Aaron Bolger's 74th-minute cross, but he was offside.
A brilliant save from Jack Brady then thwarted Rovers nine minutes later, the Town goalkeeper somehow getting a fingertip to McAllister's drive after good approach play from Kavanagh and Sean Boyd.
And Brady was there again on 87 minutes to parry away Kavanagh's curler after Boyd set up the teenager before Town struck for their winner.
Meanwhile, Jamie Doyle hit a hat-trick as Shelbourne hammered Drogheda United 7-2 in the night's other match.
Shamrock Rovers - Chencinski; O'Brien (Boyle, 60), Byrne, Gilchrist, Abulu; Bone (A Bolger, 64); Coustrain, McAllister, Kavanagh, Miele; Shaw (Boyd, 78).
Longford Town - Brady; Chambers, McDonnell, O'Reilly, Noack-Hofmann; Meehan, Hollywood (Galvin, 78), Dervin, McGlade; Verdon (Zambra 90+3), Byrne (Mulhamm, 77).
Ref - T Dempsey (Dublin)