of the season, in a 7–0 win against Willem II on 12 April 2009. During a 6–2 loss against PSV Eindhoven in a follow–up, he suffered a suspected ankle injury that saw him substituted in the 38th minute. But Emanuelson was given all clear after the medical team said his injury was not bad as first thought. Despite suffering another injury later in the 2008–09 season, he continued to remain involve in the last remaining matches and scored his fifth goal of the season, in a 1–0 win against FC Twente in the last game of the season. Following this, Emanuelson went on to make forty–two appearances and scoring four times in all competitions. Ahead of the 2009–10 season, Emanuelson was linked with a move to Bayern Munich to link up with Manager Louis van Gaal but he made it clear that he wanted to stay at Ajax. At the start of the 2009–10 season, Emanuelson continued to regain his first team place, playing in different midfield positions. Having publicly refused to play in the left–back position prior to the start of the season, he eventually played in the position following the fitness of Timothée Atouba. On 16 August 2009 Emanuelson scored his first goal of the season, in a 4–3 loss against PSV Eindhoven. He played in both legs of the UEFA Europa League Play-off round against Slovan Bratislava, as the club won 7–1 on aggregate. However, Emanuelson received a straight red card in the 81st minute for a tackle, in a 2–2 draw against Roda JC on 4 October 2009. After serving a one match suspension, he returned to the starting line–up against AZ Alkmaar on 25 October 2009 and scored his second goal of the season, in a 4–2 win. This was followed by scoring twice against FC Dordrecht and once against Feyenoord. His sixth goal of the season came on 17 December 2009 in the UEFA Europa League match against Anderlecht, as Ajax lost 3–1. On 4 January 2010, his contract talks with the club was broken down. Emanuelson said it would have been a disappointment to leave the club on a free transfer just two months prior to the contract broken down. Amid to the contract, he later scored two more goals later in the 2009–10 season against PSV Eindhoven and VVV-Venlo. In the last game of the season against NEC Nijmegen, Emanuelson set up