Dolling began playing with the Blackburn Rovers academy, before getting scouted by Manchester United's under-14 team, where he played before getting released in 2013.[2] Dolling subsequently joined Burnley, where he played with the academy team, scoring 24 goals for the Clarets at youth level.[3][4] In 2015, he joined Trafford on a short-term loan deal.[5][6]
In 2016, Dolling signed with Northern Premier League Division One North side Prescot Cables, scoring six goals in ten appearances.[7] Dolling had previously spent time on loan with Prescot Cables whilst with Burnley.[8]
In 2017, Dolling moved to the United States to play college socceratMissouri State University. In four full seasons with the Bears and a truncated 2020–21 season due to the COVID-19 pandemic, Dolling scored 40 goals and tallied 14 assists in 82 appearances. He earned All-MVC honours in all four seasons with Missouri State, MVC All-Tournament Team in 2019 and 2021, United Soccer Coaches All-American on three occasions, United Soccer Coaches All-Region on four occasions and was on the MAC Hermann Trophy Watch List in his senior year.[7]
Following college, Dolling was available in the 2021 MLS SuperDraft, but went unselected.[9]
In early 2022, Dolling signed with MLS Next Pro side St. Louis City SC 2 ahead of their inaugural season.[2][10][11] His contract option was declined by St. Louis following the 2022 season.[12]
On 23 December 2022, it was announced that Dolling would join USL Championship side New Mexico United for their 2023 season.[13] On 20 July 2023, Dolling was loaned to USL Championship side Las Vegas Lights for the remainder of the 2023 season.[14]
