Steve Holland

As a schoolboy, Holland progressed through the academy at Derby County until his late teens, when, after a bad injury, he was told that he would not be kept on. He had short stints playing professional football for Bury and for Husqvarna FF of Sweden and semi-pro for Northwich Victoria and Hyde United but, aged 21, Holland decided to go into coaching.

Crewe Alexandra

Holland was appointed as a youth coach at Crewe Alexandra in 1992 by Dario Gradi, who had coached Holland as a schoolboy. Holland had successfully completed the FA Full Coaching Licence aged 22, one of the youngest recipients of the coaching award. Holland went on to work at the club for 17 years working with young players of every age in the club's highly successful youth Academy. Holland slowly made his way through the coaching ranks at Crewe before becoming the club's Academy Director. Holland also had a spell as first team coach during the club's successful period in the Championship. At the start of the 2006–07 season, Gradi revealed that Holland would be involved more in the first team set-up for the season. On 20 April 2007, it was announced by the football club that Gradi would be taking up a new role as Technical Director on 1 July 2007 while Holland would be promoted to the role of First-Team Coach, whilst keeping his job as Academy Director. He left this role on 18 November 2008 and was replaced by former manager Dario Gradi, after which he held talks with the club to decide his future there. In December 2008, it was reported that Holland would be leaving Crewe.

Stoke City

In March 2009, he was appointed manager of the youth academy at nearby Stoke City.

Chelsea

On 12 August 2009, Holland was named the reserve team manager for Chelsea. In May 2011, Holland won the Premier Reserve League, defeating Blackburn in the…