Celtic faced First DivisionLivingston 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.
Rangers
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, 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, but the lead lasted only eight 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. Two goals from Nacho Novo and one 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 when Steven Davis passed to Novo, who shot low into the corner of the net. Boyd added the third on eight minutes after a mistake by Mallo.
Match
Team news
Celtic defender Mark Wilson returned to the squad and was named on the bench but Barry Robson missed out through injury. Strachan started Gary Caldwell in midfield alongside Paul Hartley to replace Robson. Also missing through injury for Celtic were Lee Naylor, Shaun Maloney, Paddy McCourt, Koki Mizuno and Willo Flood who was ineligible, having played for Dundee United in the semi-final. A big miss for Rangers was influential defender Madjid Bougherra with a calf injury so manager Walter Smith chose to partner Kirk Broadfoot at the back alongside David Weir. The only other absentee was Kevin Thomson who was ruled out for the rest of the season with knee ligament damage. Celtic's Glenn Loovens and Rangers' Pedro Mendes were lining up against each other having also done so in the previous season's English FA Cup Final. On that occasion, Loovens was playing for Cardiff City and Mendes for winners Portsmouth.
Match summary
After a goalless 90 minutes, the tie went to extra time. Darren O'Dea scored with a header to give Celtic a 1–0 lead, within two minutes of extra time commencing. In the last minute of extra time, Kirk Broadfoot was sent off for a professional foul on Aiden McGeady to give Celtic a penalty kick, which McGeady scored to confirm the win.
