He played 1 game in the South West Counties League in 1996/97.

Gavin Chesterfield was a youth team player at Exeter in 1998, he was part of the FA Youth Cup team that drew with Arsenal in the 4th Round.

He  played for the 1st team in the Devon Bowl against Plymouth Argyle on the 10th of May 1999.

After leaving Exeter he had a short spell at Elmore, before signing for Merthyr in 1999/2000. 

Professionally, Gavin is a UEFA A Licensed coach, who proudly works at an International level, coaching at Under 15/16 age-grade with Wales and was a part of the team that retained the Victory Shield.

Gavin is also the manger at Barry Town Utd; a position he has held successfully for around 300 senior games. He was still the manager in 2019.

In addition to these roles, Gavin works as a UEFA coach educator, mentor and assessor on behalf of the Football Association of Wales Trust (FAWT) and delivers a combination of theory and practical content across the coach education spectrum (UEFA B, through to UEFA Pro Licence).

On the 14th of June 2020, the following was reported on the Barry Town website.

"Barry Town United were delighted to announce that manager Gavin Chesterfield has agreed a new two year contract at the football club.

2020/21 will be Chesterfield’s 14th season in charge of the team, having first joined in the summer of 2007. Since then he has taken charge of exactly 450 games and become synonymous with Barry Town United.

Chesterfield won promotion from Welsh League Division Two in his first season at the helm and helped stabilise the club in the second tier. When the club were withdrawn from the league by a previous owner in 2013, Chesterfield and the Barry Town Supporters Committee fought to ensure the club’s survival and continued existence. Having won a court case, Chesterfield then guided the team to three promotions in four years, ensuring a return to the top-flight in 2017.

The revival was complete in 2019 when the club finished third in the Welsh Premier League, qualifying for European football for the first time in 16 years, something which would again be achieved this year with a fourth place finish. Chesterfield’s tenure has also included an appearance in the Welsh League Cup final in 2017 and two Welsh Cup semi-finals in 2013 and 2019.

Upon signing his new contract, Chesterfield said:

“Firstly, I want to thank the board for their continued support and belief. I’m genuinely honoured to sign a new deal with the club. Going into my 14th season we have grown immeasurably together. The future looks exciting both on and off the field and I’m proud to be a part of it.”"