Since joining Udinese, he quickly became a first-team regular, rotating in playing either at left-back or in midfield for the next five matches. After missing five matches that saw him sidelined for a month, Jankulovski returned to the first team, coming on as a 66th-minute substitute, in a 2–1 win against Empoli on 8 December 2002. He then helped Udinese keep three consecutive clean sheets between 18 December 2002 and 12 January 2003. Despite being sidelined towards the end of the 2002–03 season, Jankulovski continued to regain his first-team place, rotating in playing either left-back or in midfield. He scored his first goal for the club, in a 3–2 loss against Parma on 2 February 2003. This was followed by scoring his second goal of the season, in a 2–1 win against Piacenza. Jankulovski scored his third goal of the season, in a 3–2 win against Como on 19 April 2003. He, once again, scored two goals in two matches in the remaining two matches of the 2002–03 season against Perugia and Lazio. At the end of the 2002–03 season, Jankulovski made 29 appearances and scored five times in all competitions. Ahead of the 2003–04 season, Jankulovski's performances attracted interests from clubs at Serie A but he ended up staying at Udinese. The start of the 2003–04 season saw Jankulovski continue to regain his first-team place, rotating in playing either left-back or in midfield in the first 12 matches of the season. He played in both legs of the UEFA Cup's first round against Austria Salzburg, as the club lost 3–2 on aggregate. Jankulovski then scored his first goal of the season, in a 4–1 loss against Juventus on 9 November 2003. A month later, he scored in both legs of the Coppa Italia last 16 against Bologna, as Udinese won 4–0 aggregate. Jankulovski's fourth goal of the season came on 25 January 2004, in a 1–1 draw against Roma. He added two more goals in February, coming against Bologna and Ancona. Jankulovski added two more goals in May and saw the club qualify for UEFA Cup next season. Despite missing two matches during the 2003–04 season, he went on to make 38 appearances and scoring eight times in all competitions. In the summer of 2004, Jankulovski was linked with a move to Juventus and CSKA Moscow. Eventually, he ended up staying at Udinese, having rejected a move to CSKA