Gretna were also runners-up in the 2006 Scottish Cup. Gretna's 3–0 win in the semi-final against Dundee made them the first team from the third tier of Scottish league football to reach the final. Gretna lost to Heart of Midlothian in the final on penalties after a 1–1 draw. As Hearts had finished second in the Scottish Premier League and had therefore qualified for the UEFA Champions League, Gretna became the first team from the third tier of the Scottish league to qualify for the UEFA Cup. Gretna faced League of Ireland side Derry City in the second qualifying round, but lost 7–3 on aggregate, losing the first leg 5–1 at Fir Park, Motherwell (Raydale Park was deemed unsuitable for European football).