Dundalk FC have been relegated to the SSE Airtricity Men’s First Division after this 2-0 defeat by double-chasing Derry City at Oriel Park on Friday, on a heartbreaking night for the 14-time League Champions.

The Lilywhites were unlucky to find themselves behind just past the quarter-hour mark when Danny Mullen’s header hit the back of Colm Whelan in the six-yard box and deflected into the net.

Dundalk had Hayden Cann and Ross Munro to thank for keeping them in the game early in the second half as Cann blocked Mullen’s header on the line before his ‘keeper pushed away Sadou Diallo’s volley moments later.

Dundalk players and staff react as their side is relegated after the SSE Airtricity Men’s Premier Division match between Dundalk and Derry City at Oriel Park in Dundalk, Louth. Photo by Ben McShane/Sportsfile.

Jad Hakiki fluffed a glorious opportunity to equalise shortly after that. Munro later produced the save of the season to stop Paul McMullan making it 2-0, but within sixty seconds, the Candystripes were awarded a penalty which ex-Lilywhite Will Patching converted in the 77th minute.

Dundalk went to the end and substitute Norman Garbett went close with a header in a lively cameo appearance, but there would be no miracle fight-back as the Lilywhites’ 16-season stay in the top flight came to a very sad end after a rollercoaster of emotions over that period.

For the game, manager Jon Daly made one change to the team that drew in Galway before the international break. Paul Doyle, who is out for the remainder of the season with a broken fifth metatarsal, was replaced by Hakiki.

John Mountney of Dundalk reacts at the final whistle of the SSE Airtricity Men’s Premier Division match between Dundalk and Derry City at Oriel Park in Dundalk, Louth. Photo by Ben McShane/Sportsfile.

Derry probed in the early stages, but it would be Dundalk that had the first shot of the night when Gullan picked up possession outside the box and created room for a shot, his left-footed strike comfortable for Brian Maher in the visiting goal.

Munro was then alert to rush from his box and clear up the field as McMullan looked to pounce on a loose ball in the Dundalk half.

But Derry took the lead in the 16th minute when Michael Duffy’s corner was met by the head of Mullen whose effort hit the back of his teammate Whelan and deflected into the net. Shortly after, Adam O’Reilly let fly from distance but it bended away from goal.

Jamie Gullan of Dundalk reacts after a missed opportunity on goal during the SSE Airtricity Men’s Premier Division match between Dundalk and Derry City at Oriel Park in Dundalk, Louth. Photo by Ben McShane/Sportsfile.

In the 33rd minute, Hakiki almost broke the offside trap, but his run was just a little early as the linesman’s flag went up. Two minutes later, in a big chance, Gullan broke in on the left of the box but, from a tight angle, he drove the ball across the face of goal. Five minutes before the break, Munro saved from Whelan who had found plenty of space in the area.

At the start of the second half, Daryl Horgan’s cross was met by Hakiki whose header was straight at Maher. At the other end, Derry went close to making it 2-0 almost immediately. First, Cann blocked Mullen’s header on the line and then, in the next phase, Diallo’s volley was pushed away by a fine Munro save.

On 54 minutes, Hakiki showed good strength to brush off a Derry player and he turned and twisted in the box looking for the moment to shoot but he ended up dragging his shot wide. Moments later, Dundalk had another promising attack, but Gullan’s pull-back was behind his well-placed teammates.

Dundalk players and staff react as their side is relegated after the SSE Airtricity Men’s Premier Division match between Dundalk and Derry City at Oriel Park in Dundalk, Louth. Photo by Ben McShane/Sportsfile.

Dundalk continued to press, and Horgan’s corner was met sweetly by Robbie Benson but his goal-bound header was blocked. Ryan O’Kane and Dara Keane were then thrown on by Daly, and after a lull in the game, the manager made another double change in the 72nd minute as Mayowa Animasahun and Eoin Kenny came in.

Derry should have made it 2-0 with a quarter-of-an-hour remaining as Duffy broke down the left and squared for the in-rushing McMullan who looked certain to score but Munro produced a magnificent stop to divert the ball behind.

However, Derry were soon given the opportunity to double their advantage when Duffy was fouled in the box and up stepped Patching to plant the ball in the net.

Robbie Benson of Dundalk is consoled by Derry City manager Ruaidhrí Higgins after the SSE Airtricity Men’s Premier Division match between Dundalk and Derry City at Oriel Park in Dundalk, Louth. Photo by Ben McShane/Sportsfile.

Garbett was introduced for the final 15 minutes or so and, soon after his arrival, he was brave in the box to meet Horgan’s cross, but his header was straight at Maher, in what was Dundalk’s last real chance of the game.

Shamrock Rovers grabbed a late winner in Drogheda but that did not matter for Dundalk as the eight-point gap to their near neighbours remained with now just two games left. First Division football will return to Oriel Park next season for the first time since 2008.

DUNDALK FC: Ross Munro, John Mountney, Andy Boyle, Hayden Cann, Seán Keogh (Mayowa Animasahun 72), Koen Oostenbrink (Dara Keane 64), Daryl Horgan, Jad Hakiki (Ryan O’Kane 64), Aodh Dervin, Robbie Benson (Norman Garbett 78), Jamie Gullan (Eoin Kenny 72). Subs not used: Felix Goddard (GK), Robbie Mahon, Luke Mulligan, Scott McGill.

DERRY CITY: Brian Maher, Ronan Boyce, Mark Connolly (Duncan Idehen 79), Shane McEleney, Andre Wisdom, Adam O’Reilly, Sadou Diallo, Paul McMullan (Jacob Davenport 90+4), Colm Whelan (Will Patching 64), Michael Duffy, Danny Mullen. Subs not used: Tadhg Ryan (GK), Patrick Hoban, Seán Robertson, Aaron Heaney, Conor Barr.

REFEREE: Gavin Colfer.