Jamie Hoyland began his career at Manchester City for whom he made two appearances. When he was given a free transfer, he attempted to restart his career with Norwich. On May 21st 1986, he played for the Canaries Reserves at Wymondham Town in their Centenary Cup. Although Norwich won 3-1, Jamie was not taken on and he joined Bury making 172 appearances for them scoring 35 goals.

He then joined Sheffield United (89 games, 6 goals) before having a spell on loan to Bristol City (6 games). He joined Burnley whom he later captained and made 87 appearances for them before being released at the end of the 1997/98 season. Although he was linked with moves to Carlisle and Shrewsbury, he joined Scarborough as their new player-coach.

On 25th July 1999, the People speculated that Jamie would quit relegated Scarborough to join Hull City. The December 1999 edition of Team Talk reported that Jamie had joined rival Conference side Altrincham on a free transfer. In March 2001, Jamie was appointed youth development officer at 3rd Division Rochdale. He was promoted to Assistant Manager in June 2002.

Changes at Spotland saw Jamie demoted to a coaching role. In March 2004, he joined UniBond League First Division club Rossendale United as assistant to manager Jim McCluskie. Former Ossett Town boss Gary Brooks, who had filled the role, asked to step down due to increased demands on his time at work within the prison service. Jamie has since left his coaching duties at Rochdale.

As of September 2010, Jamie was Youth Team Manager at Preston. He then spent some time with Sheffield United's academy.

In 2017, Hoyland moved to Everton as their Head of Under-23s Recruitment.