Both teams had to play just three matches to reach the final because teams competing in Europe received a bye into the Third Round. In the semi-finals, Celtic beat Dundee United 11–10 on penalties after the match ended 0–0 following extra time. Rangers beat Falkirk 3–0 in their Semi-final
Celtic faced First Division Livingston at Celtic Park in their first match, a comfortable 4–0 victory was secured with goals from Glenn Loovens, Georgios Samaras and Scott Brown. Loovens headed into the net from a cross by Paul Caddis, Samaras added the second with a header from Loovens cross shortly after the hour. Brown added the third with a lob before Samaras got his second from the penalty spot, after Dave MacKay fouled Shaun Maloney in the penalty area. Celtic then travelled to Rugby Park to play Kilmarnock, Scott McDonald scored the opener after 10 minutes with a header, the matches first effort on goal from either side, Shunsuke Nakamura scored the second with a free-kick. Aiden McGeady ended the scoring from a Scott Brown pass, just 3 minutes after Danny Invincibile had given Kilmarnock a chance. The previous season's losing finalists Dundee United were Celtic's opponents in the Semi-final at Hampden, The match ended goalless after extra time and so was decided by a penalty shootout. An astonishing climax ensued with all 10 penalties being scored before going to sudden death. Lee Wilkie; who had missed the penalty in the previous season's final which allowed Rangers to win the cup, missed United's ninth penalty, Glenn Loovens therefore had a chance to win the match but could not score either. Another two penalties scored and it was goalkeeper time, Łukasz Załuska who would join Celtic the following season scored his and Artur Boruc did likewise, It was back to the first taker Willo Flood, who would join Celtic shortly after this match, could not convert and this time Celtic did take their chance to go through with Scott McDonald scoring the winning penalty.
As both Rangers and Celtic had been competing in Europe, they entered the competition in the third round. Rangers began their campaign against fellow Glasgow team Partick Thistle from the First Division, it was the third meeting between the two teams in two seasons, Partick had taken Rangers to a replay following a 1–1 draw at Ibrox in the 2007–08 Scottish Cup quarter-finals, a competition which Rangers went on to win.Kris Boyd opened the scoring with a stunning volley, the lead lasted only 8 minutes, with Stephen McKeown equalising for Thistle, Pedro Mendes scored the winner deep into Extra time following a goalless second half.Hamilton Academical were beaten 2–0 at Ibrox in the Quarter-final, Jean-Claude Darcheville found Kris Boyd who fired past goalkeeper Tomáš Černý after 25 minutes, Kyle Lafferty added the second from a Steven Davis cross.Falkirk were the next opponents, 2 goals from Nacho Novo and 1 from Kris Boyd ensured a 3–0 victory at Hampden Park. After eight minutes Madjid Bougherra flicked on Pedro Mendes' corner allowing Novo to finish from close range at the back post, goalkeeper Dani Mallo was beaten again five minutes from half-time, Steven Davis passed to Novo who shot low into the corner of the net, Kris Boyd added the third on 8 minutes after a mistake by the goalkeeper.