fee from Udinese. The club has been keen on signing the player since December 2004. However, he could not start playing immediately, due to a broken ankle sustained two months ago and missed the club's pre–season tour. But Jankulovski recovered and made his Milan debut, coming on as an 87th-minute substitute, in a 1–1 draw against Ascoli in the opening game of the season. Once again, he suffered another injury that saw him out for a month. Jankulovski returned to the first team from injury, coming on as a 78th-minute substitute, in a 2–0 win against Cagliari on 16 October 2005. This was followed up by making his first start for the club and setting up a winning goal for Filippo Inzaghi, in a 2–1 win against Palermo. He made his UEFA Champions League debut, coming on as a second-half substitute, in a 1–0 win against PSV Eindhoven on 1 November 2005. Following his return from injury, Jankulovski found himself in and out of the starting line-up, due to competitions he faced. He scored his first goal for Milan, in a 3–1 win against Messina on 22 April 2006. This was followed up by setting up another goal for Inzaghi, in a 2–0 win against Livorno. At the end of the 2005–06 season, Jankulovski went on to make 28 appearances and scoring once in all competitions. Ahead of the 2006–07 season, Jankulovski's future at Milan was in doubt, due to his lack of first team opportunities. But he made it clear to stay at the club. Jankulovski started the season well when he helped the club keep six consecutive clean sheets between 13 September 2006 and 1 October 2006. During which, Jankulovski scored his first goal of the season, scoring the only goal of the game, in a 1–0 win against Ascoli on 20 September 2006. He then scored his second goal of the season, once again, scoring the only goal of the game, in a 1–0 win against Chievo on 25 October 2006. Since the start of the 2006–07 season, Jankulovski quickly established himself at left-back. Upon the arrival of with Massimo Oddo, he became one of Milan's best players, and together, they were relied upon when the club lacked traditional wingers among the attacking players. On 11 February 2007, Jankulovski scored from 25 yards, which turns out to be a winning goal, in a 2–1 win against Livorno.