Career
Chaplain began his career in the Rangers youth set-up before moving on to Ayr United in 2000. He made 91 starts and scored 11 goals in his 5 seasons at the club before being released and signing for Albion Rovers. At the end of the season, he was snapped up on a full-time contract by Partick Thistle manager Ian McCall.
After leaving Partick Thistle in the summer of 2009, Chaplain was signed by Dumbarton.
He signed for a second stint with Albion Rovers in January 2011, helping them to an against-all-odds promotion into the Second Division. He scored the goal that got Rovers into the play-off final, and in that final against Stranraer he scored two goals to help Rovers to a historic survival in the third tier.
In Summer 2012 Chaplain left Albion Rovers on that high for a stint with Third Division side Annan Athletic but could not resist a move back to Cliftonhill in May 2013. After helping Rovers to a league title, Chaplain retired from football on 3rd June 2015 having been offered a position with the Scottish Football Association.