Holland- Assistant First-Team Coach.

Holland was delegated as an adolescent mentor at Crewe Alexandra in 1992 by Dario Gradi, who had trained Holland as a schoolboy.in 2006, he entered onto the UEFA Pro License course and finished it in June 2007. He additionally finished the “LMA PFA” Certificate in connected administration at Warwick University in 2009.

 Holland gradually made his direction through the honing ranks at Crewe before turning into the club's Academy Director, caring for the club's fruitful academy. The Academy prepared an assembly of players who went onto play at the most elevated level. Holland additionally had a spell as first group mentor throughout the clubs fruitful period in the Championship. 

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Holland might be leaving Crewe in March 2009, he was selected administrator of the young foundation at close-by Stoke City on 12 August 2009, and Holland was named the store group boss for Chelsea in flavor 2009-10.  Holland was part of the Chelsea administration group that won the Domestic Double, for the first run through in the clubs history. Now Holland would fill the role of assistant first-team coach.