The Third Round draw was conducted on 27 October 2008. Six matches were postponed, all because of frozen pitches. They were rescheduled for the following Saturday. However, only two of those matches were played on that day,
Elgin City v
Spartans and
Forres Mechanics v
Dalbeattie Star. The other matches were repeatedly postponed because of poor weather. The
Edinburgh City v
Brechin City tie was eventually played on 8 December 2008 and the
Inverurie Loco Works v
Vale of Leithen tie on 13 December 2008. The
Lochee United v
Ayr United match was played on Tuesday, 23 December 2008. On 11 December 2008, the match between Elgin City and Spartans was ordered to be replayed after Elgin had fielded Joe Malin, a loanee from
Ross County, in a 2–1 win. Malin was not registered in time for the original tie, but played in the rescheduled tie. The match was ordered to be played on 15 December. It later emerged that Spartans had also fielded an ineligible player, Dean Hoskins, after an administrative error. Source: ESPN Soccernet:[https://archive.today/20130103074440/http://soccernet.espn.go.com/scoreboard?league=sco.tennents&date=20081206&refresh=0&cc=5739, [https://archive.today/20130103124017/http://soccernet.espn.go.com/scoreboard?league=sco.tennents&date=20081213&refresh=0&cc=5739
Replays Source: ESPN Soccernet: [https://archive.today/20130102220309/http://soccernet.espn.go.com/scoreboard?league=sco.tennents&date=20081215&cc=5739, ==Fourth round==