Shortly after, he signed a new contract with Milan, keeping him until 2011. Jankulovski helped the club keep three consecutive clean sheets between 28 April 2007 and 6 May 2007, including a 3–0 win against Manchester United in the second leg of the UEFA Champions League that sent the club into the final. On 23 May 2007, he took part, starting at left-back and contributed to Milan's 2–1 victory in the final of the UEFA Champions League against Liverpool. After the match, Jankulovski said: "I can't even describe how I feel. It's beautiful. You could say it was random, but then we believed we could do it. It helped us, we were ahead of the half and we knew Liverpool had to open the game. This was confirmed and we finally added a second goal. Especially in the first half, they were better. I wasn't in the team at the time, but the memories are still alive. Fortunately, we've done it now." La Repubblica commentened on his performance, saying: "The crooked things of a Milan that travel under the track are all his. Benítez, on the left wing, organized an uncomfortable saucer for him, Pennant going, Mascherano introducing himself and looking for contrast." Despite being sidelined on five occasions throughout the 2006–07 season, Jankulovski made fifty appearances and scoring three times in all competitions. At the start of the 2007–08 season, Jankulovski started at left-back against Sevilla in the 2007 UEFA Super Cup held on 31 August 2007 and scored the second goal of Milan's victory with a volley following a pass from Andrea Pirlo. He then regained his first-team place, playing at left-back in the first two months to the season. Following a 1–0 loss against Empoli on 21 October 2007, Jankulovski suffered a knee injury and was expected to be out somewhere between two and six months. In early December, he made a recovery from injury and made his return to the first team against Urawa Red Diamonds in the semi-final of the FIFA Club World Cup and helped the club keep a clean sheet to win 1–0 to advance to the final. Despite appearing as an unused substitute, Milan went on to win the tournament after beating Boca Juniors 4–2 on 16 December 2007. However, his return was short-lived when Jankulovski suffered a knee injury that kept him out for two months. He made his return to