Jamie started his youth career at Swansea City and during his time with The Swans, had loan periods at Haverfordwest County and Forest Green Rovers. Spells at Redditch United and Bedford Town would follow before making the switch to Conference Premier side Kidderminster Harriers.
During a two year association with the Aggborough club, Grimes would go on to make over 60 appearances before moving to Dover Athletic. Jamie would become a regular for The Whites and captained the side before making the step up to League 2 side Cheltenham Town. During the 2017/18 season, Grimes went on to be an ever present for the Whaddon Road side and was given the role of vice-captain during his season there.
In June 2018, Grimes signed a one year deal with Macclesfield Town Football Club.