Chygrynskiy earned his debut in the Ukrainian Premier League in 2004, at the age of 17. In 2005, he was loaned out to Ukrainian club Metalurh Zaporizhzhya, where he experienced continuous top flight football. After a successful stint at Metalurh, Dmytro was brought back to Donetsk. He quickly emerged as a consistent defender and a leading figure, and first experienced Champions League football when coming on as a substitute against FC Barcelona during the 2004–05 UEFA Champions League. The young player cemented a starting position at the team in the 2006–07 season, by the end of which, at the age of 20, he captained Shakhtar in the Ukrainian Cup final against Dynamo Kyiv in the absence of the regular captain, Matuzalém.