2008-09: Dan Milan played 26 games as a junior for Orchard Lake St. Mary's Prep in Michigan. He scored 5 goals with 4 assists.
2009-10: Milan was a team captain for Orchard Lake St. Mary's Prep and was named All-State after scoring 5 goals with 13 assists in 31 games. Milan was selected by the Des Moines Buccaneers in the seventh round (93rd overall) of the 2010 USHL Entry Draft but chose to join Moncton in the QMJHL.
2010-11: Milan skated in 68 games for the Moncton Wildcats and was named to the QMJHL All-Rookie team as an 18-year-old. He scored 14 goals with 24 assists and was -26 with 76 PMs. Milan skated in all five playoff games for the Wildcats and was -1 with 1 goal, 1 assist, and 5 PMs. He signed a three-year, entry-level contract with Tampa Bay in September, 2011.
2011-12: Milan did not enjoy the same success of his rookie season in his second year in the QMJHL. After putting up 38 points for Moncton the previous year, he had 5 assists and was minus-13 with 31 penalty minutes in 33 games with the Wildcats before being traded to Victoriaville at the January trade deadline. Going from middle-of-the-pack Moncton to the Tigres, who finished second in the East Division and had the QMJHL's third best record, didn't change things much. Milan scored 2 goals with 4 assists and was minus-three with 42 penalty minutes in 29 games. He played in 3 of 4 playoff games and was minus-two with no points and 2 penalty minutes as Victoriaville was swept by Baie-Comeau.
2012-13: Milan skated for the ECHL's Florida Everblades in his first pro season. In 43 games he scored 2 goals with 7 assists and was +5 with 56 penalty minutes. A healthy scratch at times in the beginning of the year due to a surplus of defensemen, he scored 2 goals with 7 assists and was +5 with 56 penalty minutes. The Everblades lost to Kelly Cup champion Reading in the Eastern Conference semifinals. Milan did not appear in any playoff games.