He has previously worked as a manager at Leeds United, Forest Green Rovers, Kidderminster Harriers and in a caretaker capacity at Coventry City.

In his final season in Lancashire, he made 40 league appearances and scored eight goals, but was unable to prevent Blackpool from finishing fourth from bottom and needing to seek re-election.

He was a member of the Shrewsbury team who won the Third Division title at the end of his first season, before he dropped out of league football, moving to Cirencester Town in 1995.

[citation needed] In 1996, Hockaday established one of the first football academies in the country at Cirencester,[4] following the Thorp Arch model that Howard Wilkinson started at Leeds United in 1994.

As Under 18 coach at Watford, Hockaday helped develop the careers of players such as Paul Robinson, Hamer Bouazza, Tommy Smith, Darren Ward, Ashley Young and Alhassan Bangura.

[8] On 19 June 2007, it was announced that he would be joining Southampton as youth team coach replacing Georges Prost,[9] he was put on gardening leave by the club in January 2009 and was released from his contract in May of the same year.

Despite the team finishing in a relegation position and coming under fire from a number of the club's fans, Hockaday was offered a new one-year contract for the 2010–11 season.

Hockaday's fourth season as manager of the club again ended with another 10th-place finish in the Conference Premier despite reportedly having the largest transfer and wage budget in the division.

[19] In February 2013, Hockaday dismissed rumours linking him with the vacant managerial post at former club Swindon Town after the departure of Paolo Di Canio.

[20] After a disappointing start to the 2013–14 season, and after a run which saw Forest Green suffer seven defeats in eight games, Hockaday left the club by mutual consent on 21 October 2013.

[25] Hockaday took his team to Italy for a two-week training camp, and his first pre-season game as head coach resulted in a 16–0 victory against Italian amateur minnows FC Gherdeina.

After the sixteenth goal had been scored, United's new goalkeeper Marco Silvestri was allowed to switch sides and play for the amateur team until the end of the game.

[28] Hockaday's first and only league victory was against Middlesbrough at Elland Road on 16 August, with new striker Billy Sharp scoring a late winner on his debut.

[31] After the Watford game, Leeds United's owner Massimo Cellino was reported to have made up his mind to sack Hockaday, but then had a change of heart, deciding to blame himself for the club's poor start to the season.

[36] Later that month, he took on the role of assistant manager at Swindon Supermarine on a temporary basis, with club director Jez Webb describing Hockaday's appointment as "humbling.

"[37][38][39] Following his temporary role with Swindon Supermarine, Football League One side Coventry City announced on 2 February 2015 that Hockaday had been appointed professional development coach for the rest of the 2014–15 season.