He then moved back to Tasmania and coached the Tasmanian Devils in the VFL. Cresswell's brother Shane had coached Ulverstone (NTFL) to the premiership in 2000. In 2009 Cresswell was appointed player coach of Division One Sydney AFL side the Manly Wolves. Despite a promising start to the season, numerous off-field issues -including being extradited to Queensland for fraud- and player discontent saw Cresswell sacked from the role at season's end. In April 2009 he was declared bankrupt, owing almost $700,000. He admitted that a gambling addiction had led him to lose everything after he retired from playing football. 2010 saw Cresswell sign with Sydney AFL Premier Division side Western Suburbs, kicking 33 goals in 10 matches. In December 2010 Cresswell was found guilty of fraud offences and sentenced to a minimum 10 months jail. Upon release in October 2011, he appeared on Channel 7's "Sunday Night", where he admitted to placing a $200 bet on a match he was playing in back in 2003.