Career
Although born in England, he has played internationally for Wales. He has previously played for Heart of Midlothian, East Fife and Wrexham. Hearts
Ogleby was with Coventry City as a youth, but was released by them after two years.
He signed for Heart of Midlothian (Hearts) in 2010 and initially played for their under 19 squad.
He was promoted to the first team on the final day of the 2010-2011 season, but did not make an appearance in the match against Dundee United. At the start of the 2011-2012 season, Ogleby was sent on loan to East Fife to gain first team experience.
On his return to Hearts he went on trial with Falkirk with a view to a further loan. The loan deal never materialised and on 31 January 2012 he negotiated early release from his Hearts contract.
East Fife (loan)
Having yet to break into the Hearts first team Ogleby joined East Fife on loan on a six-month deal in July 2011.
Making his debut in a friendly against parent club Hearts. He went on to make his league debut on 6 August against Stirling. Due to match call off"s in December, appearances were limited and his last game came on 2 January against Cowdenbeath.
In all he made 19 appearances in all competitions scoring 8 times before returning to Hearts.
Wrexham
After his release from his Hearts contract he joined Conference National side Wrexham on a 3-month deal. He was given the number 31 shirt.
Ogleby was given a new contract at Wrexham ahead of the 2012/13 and given the number 15 shirt, he played a large part in Wrexham"s pre-season matches, He scored goals in games against Aberystwyth, Kilmarnock, Bala Town and Coventry City. In the opening game of the 2012/13 Conference season Ogleby scored Wrexham"s first goal of the League campaign with a superb goal at the Racecourse against Woking in a 3–1 victory.
He picked up his first career honour in March 2013 winning the FA Trophy with the North Wales club
On 1 May 2014, Ogleby was released by Wrexham. Livingston
Ogleby signed for Livingston in July 2014. Nuneaton Town
In January 2015, Ogleby joined Nuneaton Town.
He made his debut on 17 January 2015 in a 0-2 home loss to Gateshead.
Leamington
On 22 May 2015 it was announced that Ogleby had signed with Southern League outfit Leamington F.C.
He made his debut for Wales U21 on 27 November 2010 against Austria. He went on to appear against Northern Ireland on 9 January scoring in only his second appearance.
Wrexham
FA Trophy 2012/2013.