Career
Bradford City and Huddersfield Town
Born in Bradford, West Yorkshire, Chippendale played for hometown club Bradford City in their youth system before being released at the age of 13 when he joined Huddersfield Town. He was promoted to the first team squad for a game against Colchester United on 3 October 2009. = York City (loan) On 25 March 2011, he joined Conference Premier club York City on loan until 30 April.
After not being involved in any matches during his first month at the club, Huddersfield manager Lee Clark recalled Chippendale from his loan on 19 April 2011.
= Inverness Caledonian Thistle (loan) On 31 August 2011, Chippendale joined Scottish Premier League side Inverness Caledonian Thistle on loan until January 2012. He made his debut for Inverness on 10 September 2011 as an 81st-minute substitute against Hearts at the Caledonian Stadium in a 1–1 draw.
He returned to Huddersfield on 9 January after his loan expired. He left Huddersfield club in June 2012, after not being offered a new contract by manager Simon Grayson.
Accrington Stanley
Chippendale signed a one-year contract with League Two side Accrington Stanley after a successful trial on 25 July 2012.
He made his debut for Accrington in a League Cup fixture on 11 August 2012 against Carlisle United in a 1–0 loss at Brunton Park. Chippendale was released by Accrington Stanley in May 2013 after struggling to make an impact and only starting four games for the club Bury
On 23 July 2013, Chippendale signed a one-year contract with League Two side Bury after a successful trial.
On 5 November 2013, Bury confirmed that Chippendale"s contract had been cancelled by mutual consent.
= Chester (loan) On 23 August 2013, Chippendale signed on loan for a month at Chester. AFC Fylde and Ashton United
Following his departure from Bury, Chippendale signed for AFC Fylde in December 2013 Then joining Ashton United for the remaining of the 2013-2014 season.
Stalybridge Celtic
In July 2014 he joined Stalybridge Celtic.