| Season | Club |
| 2000/01 | Celtic U17 |
| 2001/03 | Blackburn U18 |
| 2003/04 | Blackburn, Huddersfield (loan), Blackburn |
| 2004/05 | Blackburn, Bury (loan), Blackburn |
| 2005/06 | Blackburn, Blackpool (loan), Blackburn |
| 2006/07 | Grimsby Town |
| 2007/09 | Partick Thistle |
| 2009/11 | Dundee |
| 2011/12 | Kilmarnock |
| 2012/13 | Kilmarnock, Dundee |
| 2013/14 | St. Mirren, Oldham Athletic (loan), St. Mirren |
| 2014/16 | Dundee |
| 2016/17 | Ayr United |
| 2017/18 | Greenock Morton |
| 2018/19 | Queen of the South, Partick Thistle |
| 2019/20 | Partick Thistle, Stenhousemuir |
| 2020/21 | Gartcairn |
| 2021/22 | Forfar Athletic (player coach) |
| 2022/23 | Kilbirnie Ladeside (player coach) |
| 2023/24 | Glenafton Athletic (player / assistant manager) |
| Gary left the club 19/10/2023 |
Glenafton Athletic 