At the start of the 2007–08 season, Jankulovski started in the left–back position 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 in the left–back position 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 to six months. But in early–December, he made a recovery from injury and made his return to the first team against Urawa Red Diamonds in the semi–finals 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 the first team from injury against Siena on 10 February 2008 and started the whole game to help the club a clean sheet, in a 1–0 win. Following this, Jankulovski continued to be involved in the first team despite suffering further injuries later in the 2007–08 season. At the end of the 2007–08 season, he went on to make nineteen appearances and scoring once in all competitions. Following this, on 28 May 2008, Jankulovski was named the 2007's Czech Player of the Year , with Petr Čech coming in second place.