The left-sided defender/midfielder-joined Whitby Town from Newcastle Blue Star in September 2008 and made his debut on the 20th September 2008 in a 4-2 away victory over Leigh Genesis. Leon's first goal for the club was an 88th minute winner in a 3-2 victory over Trafford at the Turnbull Ground in an FA Trophy 1st qualifying round tie on the 18th October 2008. He went on to make 33 appearances scoring five goals that season before joining Harrogate Town in June 2009.

Leon returned to Whitby on loan from Harrogate Town in October 2009 and made his second debut for the club on the 10th October 2009 in a 1-0 victory over Marine at the Turnbull Ground but was sent off after 75 minutes. He re-signed from Harrogate Town and went on to make a total of 106 appearances scoring eight goals before leaving and joining Shildon in June 2011. Leon played over 200 games for Darlington between 2012 and 2018 winning the Northern League 1st Division in their 1st season as Darlington 1883 and was a regular in their midfield in their 2014/15 and 15/16 promotion winning season’s before signing for Scarborough Athletic in August 2018, but after failing to keep a regular place in their side Whitby manager Chris Hardy brought him back to the club in November 2018, handing him his third debut for the club in the 2-1 away victory over Hednesford Town on Saturday 8th December 2018. Leon scored two more goals for the club, the opening strike in the 5-2 away defeat at South Shields and the equaliser in the 1-1 draw at the Turnbull Ground v Lancaster City on the 9th February 2019 going on to make a further 21 appearances before the 2018/19 season ended. His last game for Whitby saw Leon come off the bench in the final match of the season a 2-1 away defeat at Lancaster City on Saturday 27th April 2019, where unfortunately he was sent off in the dying moments of the game. Leon was released by the club at the end of the season and joined Marske United after making a total of 127 appearances, scoring ten goals for Whitby Town.

Whitby came across as very homely and very friendly. They were not small in terms of ambition but a very tight a very friendly style of club. It sounds a little bit daft, but it's like my Nana's home - very warm, very loving with nothing that made me feel uncomfortable or out of place. I was welcomed by everyone and treated the same way by everyone. I felt at home.

Graeme Clark was the first person to bring me in. I was trying to think the other day how many years I did with Whitby, it was my second longest stint after Darlington. I received a call when I was at Newcastle Blue Star. Cammy and people like that were there back then, I was just 19 or 20. It was a nice club and nothing really ever went wrong. I felt that it was a club that's got potential to kick on with that bit more backing. It was a challenge to me to help take Whitby somewhere. I knew they won the Vase with Graham Robinson and Andy Toman. I knew they were a long-serving club in that league. Macca was there, but the ones that stick out the most were Jimmy Beadle, the Gildea brothers, Fozzie at centre half, Tony Hackworth, Ged Dalton, and the Harry Dunn era overall. They were probably my most successful times at Whitby Town. I won the players' player award and I've still got that. I think that was my first real personal non-league achievement.

[Before my final spell at Town] I got a call from Chardy. He gave me a bit of a brief of what he wanted and I fitted the bill. I was more than happy to come back. I knew what the club was all about. It wasn't far from me, and Chardy's input swung it for me - he wanted to push on and just leaving Scarborough, I wanted to get one over on them. One of my best memories was beating them on New Year's Day. I'd be lying if I said I didn't check the fixtures and see if Whitby still had Scarborough to play. It worked out perfectly. I remember after the game, Steve Kittrick, their manager, said "why didn't you play like that every week for us?". He held his hands up, said he got it wrong and wished me all the best at Whitby.