Dow began to play more regularly after Jackie McNamara became Dundee United manager in 2013. He was selected to start in the first match of the 2013–14 season, ahead of more established players like Gary Mackay-Steven. As the season progressed, Dow was often selected in the middle of a front three formation, despite strong competition for the attacking positions in the team. He later had an extended run in the first team and scored his first goal of the season, in a 3–1 win over Motherwell on 21 February 2014. His second goal came on 26 March 2014, as Dundee United beat Inverness 2–1. Then, on 26 April 2014, Dow scored his third goal of the season in a 5–1 win over Motherwell. On 13 May 2014, Dow signed a new contract until 2016, ending three months of negotiations. A few days after signing his new deal, Dow started in the Scottish Cup Final, as Dundee United lost 2–0 to St Johnstone.