Dundalk have participated in the FAI Cup since 1927, when Bohs inflicted a 6-1 defeat in Dalymount Park.
The following season Dundalk met Shels for the first time, the Reds prevailing on 3-1 scoreline in Dublin. It was 1932 before they met again in a first round match; Shels again winning, 2-1. Peter Kelly getting the consolation goal for the Lilywhites.
The next pairing came in 1941 in the second round. Goals from Jimmy McArdle, Joey Donnelly, Paddy Barlow and Henry Hurst earning a 4-4 draw. The replay in Oriel ended at three goals apiece after a pitch invasion. Donnelly, McArdle and a penalty from Tom Crawley insured a second replay, which Dundalk won 2-0, Charlie Reid and Harry Bryan netting.
In 1942 Dundalk won the cup for the first time in the club’s history, beating Cork United 3-1, Artie Kelly (2) and Johnny Lavery scored in front of a 34,298 crowd in Dalymount. On the way to the final Shels were defeated 2-1 away, Barlow and Lavery on the mark. Four locals lined out in the final - Billy O’Neill, Tom Crawley, Joey Donnelly, the captain, and Jimmy McArdle.
1944 saw them paired in a two leg semi final, Shels winning 4-2 on aggregate after a draw in Oriel Park. Donal Flanagan scoring for Dundalk. Paddy Barlow got the only goal in a 3-1 away defeat.
Shels, who had helped Dundalk after a fire in Oriel Park with a kit for the semi final lost 3-2 to Rovers in the final. Shels recorded their biggest cup win over Dundalk in 1948 with a first round 5-1 drubbing. The following year, 1949, saw them clash for the first time in the final, with Dundalk capturing their second Cup with a 3-0 victory. Jackie Walsh and Ronnie Henderson scoring. The Shels side had Dermot Keely’s father Peter and Sean Haughey, brother of Charlie, in their line up.
The two teams met in the 1958 cup semi final where a Vincie Gilmore goal saw Dundalk through to a final date with Shamrock Rovers. Red hot favourites, Rovers were shocked by a very determined Dundalk side who had struggled all season.
The swinging sixties saw the sides meet just once - a 1960 semi final joust which Shels won 4-1, Ted Harte scoring for Dundalk. Shels went on to lift the cup, beating Cork Hibs 2-0 in the final. Tony Dunne the great Man United full back played his last game for Shels that day.
A John Delamere goal sent Dundalk packing in the first round in 1984. in 1989 goals from Paul Newe (2) and John Cleary beat Shels 3-1 in a second round tie, before losing in the quarter finals 1-0 to Cork City in a replay, Patsy Freyne scoring. For only the second time they met in a final, the 1993 decider going Shels way thanks to a Greg Costello goal.
This brought Turlough O’Connor’s eight year reign as Dundalk manager to an end. On their way to winning the 1997 cup against Derry Shel beat Dundalk 4-2 in Tolka Park, Brian Byrne and Joe Gallen getting Dundalk’s goals. The next season Shels needed a replay in the second round to beat Dundalk 2-0. The most recent pairing came in 2008 with Dundalk winning 3-0 in Tolka.