In June 2005, Hleb joined English side Arsenal for a sum which had the potential to reach €15 million, on a four-year contract. Arsène Wenger used Hleb at many different midfield positions, but he mainly played on the right wing for Arsenal. His competitive debut was made in August 2005 against Chelsea in the 2005 FA Community Shield, and then he made his league debut as a substitute against Newcastle United. Soon after, Hleb sustained a knee injury while on international duty with Belarus and was out for several months, returning to the first team squad in December, and played 60 minutes in Arsenal's final UEFA Champions League group stage match against Ajax on 7 December. By January 2006, Hleb had established himself as a first choice player and scored his first goal for Arsenal in a 7–0 win over Middlesbrough. In May, Hleb became the first ever Belarusian footballer to play in the Champions League final. He ended the season with 40 appearances and three goals.