2008–09 Dumbarton F.C. season

Jim Chapman's first full season in charge began with a large intake of new playing staff.

A slow start however was to be replaced by an unbeaten run of 8 games which saw Dumbarton rise to 2nd place by the beginning of November.

Mixed results in December through February meant that Dumbarton fell to 4th place, but still in with a playoff chance.

In the Scottish Cup, a second round victory over Highland League opponents Fraserburgh was followed by a close encounter with First Division Ross County, which was only decided by the odd goal in three and that after a draw.

In the League Cup, Dumbarton defeated Annan Athletic on penalties, but were to be overwhelmed by Premier Division St Mirren in the second round.