Career
Pailan Arrows
During the summer of 2010 Singh signed with Pailan Arrows who were then AIFF XI in the I-League. He scored his first goal for the team against his former club East Bengal on 26 February 2011. After the 2010-2011 season Singh reportedly went back to East Bengal but was rejected during pre-season and ultimately ended back at Pailan Arrows for the 2011-2012 season.
He scored his second ever goal for Pailan Arrows on 3 December 2011 against Mumbai F.C. in the I-League.
= 2012-2013 season Singh began the season for Pailan Arrows during their first official tournament, the 2012 Durand Cup, with a goal in his first game of the season against Delhi United in the first match of the tournament for Pailan Arrows to help Arrows draw 2–2. Singh then played in two of the three matches for Pailan Arrows in their second tournament, the 2012 Indian Federation Cup.
Singh then opened his 2012-2013 I-League campaign with a goal from the penalty spot as Pailan opened their campaign with a victory which was also the first I-League victory for new coach Arthur Papas. Pailan however went on a run of bad form during the month of November and for Singh the month was summed up after he received a yellow card in Pailan"s 3–1 loss to Shillong Lajong F.C. on 28 November 2012.
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 Oil and Natural Gas Corporation F.C. in which Singh scored in the 57th minute from the penalty spot.
Singh then scored again for Pailan Arrows on 22 December 2012 against Dempo from the penalty spot again but that was not enough as Pailan fell 2–1 to the reigning champions. Shillong Lajong
On 19 May 2013, media revelaed that Milan is going to join Shillong Lajong for next two-year. He made his debut for Shillong Lajong in the I-League on 22 September 2013 against Dempo South Carolina (U.S.) Milan represented North East United Football Club during the 2014 ISL.