Jonathan began his career with his local club Ballybofey United in the East Division of Donegal Schoolboys League. Selected for the Donegal Schoolboys 1992 League Centre squad and played in the 2005 Kennedy Cup. Was a member of the Donegal Schoolboys U-16 side which played in the Inter League Final in 2009. Capped by the Republic of Ireland at U-15 and has played at every level up to U-21 since then. Joined Wolverhampton Wanderers in May 2009 on a 2 year contract making his debut for the Reserves in January 2010. A metatarsil injury hampered his progress over the next year and he eventaully went out on loan to Barnet in the English 2nd Division where he made his full league debut in January 2011. Joined Cork City in the Airtricity League Premier Division at the start of the 2012 season and after two full seasons with the Leesiders was made captain for the 2014 season. Captained the City in the FAI Irish Mail Cup Final defeat to Dundalk in 2015.