At the beginning of the 2008–09 season, Chygrynskiy helped the squad win the Ukrainian Super Cup. With Shakhtar, he played in the group stage of the UEFA Champions League, finishing third in the group behind Barcelona and Sporting Clube de Portugal. This was not the end of the club's European journey, however, as they parachuted down to the UEFA Cup. He helped them team make it to the quarter-final stage, defeating 1993 European Champions Olympique de Marseille. They then progressed to the semi-finals, where they played Ukrainian rivals Dynamo Kyiv. Shakhtar progressed to the 2009 UEFA Cup Final against DFB-Pokal champions Werder Bremen – Chygrynskiy and Shakhtar won the trophy 2–1 after extra time.