Dolan began his career at Middlesbrough and in July 2010 was awarded a four-year professional contract with the club, and was captain of their U21 side. On 4 January 2013, Dolan joined Football League One side Yeovil Town on a months loan deal, and made his debut as a substitute in their Football League Trophy area semi-final defeat against Leyton Orient. He played his first League One match for the club in the 2–0 win at Sheffield United. Dolan only managed five appearances for Yeovil in his first spell on loan before returning to the Riverside due to injury. On 27 March 2013, Dolan unexpectedly returned to Yeovil for a second loan spell this time until the end of the 2012–13 season. On 29 March 2013, Dolan made his first appearance of his second loan spell for Yeovil as a second-half substitute in a goalless draw against Walsall. On 1 April, he scored his first goal in professional football in the 2–1 away win at Notts County, with a goal scored direct from a free kick. Dolan appeared as a second-half substitute in the 2013 League One play-off Final as Yeovil beat Brentford 2–1 to secure promotion to the Football League Championship. Dolan returned to Middlesbrough having made 9 appearances for Yeovil in a loan spell hampered by injuries. In August 2013, Dolan joined his home-town team Hartlepool United on a one-month loan deal, linking up with former Middlesbrough coaches Colin Cooper and Craig Hignett. This loan was extended in October. Dolan then scored his first goal for the club, in a 3–1 win over Wimbledon on 22 October 2013. This was followed up his second came on 26 December 2013, in a 1–1 draw against Chesterfield. Dolan returned to Hartlepool United in January after making 20 appearance and scoring twice for the club. Under the management of Aitor Karanka, Dolan was the among players to be offload as part of Karanka's reducing the squad size. So on 1 September 2014 Dolan agreed to join Bradford City on loan until the end of the season.
Bradford City
On 6 May 2014, Dolan agreed to join Bradford City on a one-year contract. He moved on loan to Hartlepool United on 27 November 2014. He only made 2 appearances when he was recalled to Bradford City due to an injury.
Yeovil Town
Following his release from Bradford City, Dolan agreed to sign for League Two side Yeovil Town on a two-year deal from the 1 July 2015.
Newport County
On 7 June 2017, Dolan rejected the offer of a new contract from Yeovil to sign for fellow League Two side Newport County on a two-year contract. He made his debut for Newport on the opening day of the 2017–18 season, in a 3–3 draw at Stevenage. On 10 November 2017 Dolan scored his first goal for Newport in the 1–1 draw against Port Vale in League Two. On 26 January 2019 Dolan scored the equalising goal in the 93rd minute against Championship club Middlesbrough in the FA Cup 4th round 1–1 draw. Newport won the replay 2-0 and progressed to the FA Cup 5th round home tie against reigning Premier League champions Manchester City. Manchester City won the match 4–1. Dolan scored the winning goal in the 2018-19 League Two playoff semi-final penalty shoot-out against Mansfield Town In the League Two playoff final at Wembley Stadium on 25 May 2019 Newport lost to Tranmere Rovers, 1-0 after a goal in the 119th minute. In June 2019 Dolan signed a two-year contract extension with Newport County.
