a follow–up match against Vitesse, he scored his first goal of the season, in a 2–2 draw. By February, Emanuelson began primarily played as a left midfielder because of his weak defending abilities and Jan Vertonghen took over the position. The player, himself, publicity said he does not want to return to the left–back position. Emanuelson then scored two goals in two matches between 24 February 2008 and 2 March 2008 against NAC Breda and SBV Excelsior. However, he eventually played in the left–back position against SC Heerenveen in play–offs for the UEFA Champions League spot, as Ajax won 5–2 on aggregate. In a follow–up match against Twente, Emanuelson suffered ankle injury that saw him substituted in the 66th minute, as the club lost 2–1. As a result, Ajax lost their chance to qualify for the UEFA Champions League following a 0–0 draw in the return leg. At the end of the 2007–08 season, he went on to make forty–one appearances and scoring three times in all competitions. At the start of the 2008–09 season, Emanuelson started in the first three matches, playing once in the centre–midfield position and twice in the left–back position before missing two matches due to illness. He returned to the starting line–up against SC Heerenveen on 5 October 2008, and played the whole game, as Ajax lost 5–2. Emanuelson then contributed five assists for the club by the end of the year. On 21 December 2008 he scored his first goal of the season, in a 6–0 win against De Graafschap. By November, Emanuelson began playing in different midfield positions for Ajax. But at one point, he did play in the left–back position against NEC Nijmegen on 18 January 2009, as the club won 4–2. His second goal of the season came on 15 February 2009, in a 2–0 win against rival, Feyenoord. After missing one match due to a stiff neck Emanuelson sustained during a UEFA Cup third round first leg against Fiorentina and set up the only goal of the game in a 1–0 win, he returned to the starting line–up in the return leg against them and helped the side go through to the next round following a 1–1 draw. By March, Emanuelson then publicly criticised Manager Marco van Basten for his substitution policy after he was substituted five times in the last eight league matches. Emanuelson then scored his third goal