Raymond started his career with local side Castlefin Celtic and was a permanent fixture in Eunan Brolly's 1993 League Centre squad. Joined Finn Harps in 2011 and played regularly with the U-19 side before breaking into the first team towards the end of the season. Made the move to Derry City in 2012 to obtain more game time before going out on loan to Ballinamallard United in the Irish League Premier Division in 2013. Returned to Finn Park as one of Ollie Horgan's new signings at the start of the 2014 season and established himself in the middle of the park helping Harps gain promotion to the Premier Division in 2015. Moved to Institute in January 2017 as they pushed for promotion to the Irish League Premier Division.