[5] Singh then scored his second goal of the season, again from the penalty spot, in the 69th minute against Air India on 11 October 2012 to help Pailan Arrows win the match 2–1.
[7] Singh then began the month of December in fashion by putting in a man of the match performance for Pailan Arrows in a 4–1 victory over ONGC F.C.
[13] Indian Super League opportunity came calling again for Milan as he was signed on loan by the Delhi-based ISL side.
On July 18, 2016, Delhi Dynamos announced that Milan would be joining the side for 2016 edition of the Indian Super League [14] Coached by Italian legend and World Cup winner Gianluca Zambrotta, Milan made 15 starts for the side scoring 2 important goals against Pune City FC & Atletico de Kolkata.
[15] He had a standout ISL as Delhi Dynamos made it to the Semi-Finals while Milan was regarded as one of the stand-out Indian players in the league [16] On 23 July 2017, Singh was selected in the 5th round of the 2017–18 ISL Players Draft by the Kerala Blasters for the 2017–18 Indian Super League season.