Cresswell started his football with Glenorchy in the Tasmanian Football League. He also briefly played for Geelong Reserves in the Victorian Football League, Daryn then returned to Tasmania to play with North Hobart in the TFL the following year. Daryn was then drafted to the Sydney Swans in the mid-season draft. Cresswell played for the Swans for twelve seasons between 1992 and 2003, playing 244 games, the seventh most games in Sydney and South Melbourne history. He was a member of the Swans losing 1996 Grand Final team and was named in both the Swans and Tasmanian Teams of the Century. In 1993, in his second season he won the Swans most improved award and the following season he was awarded the Bob Skilton Medal as the Swans best for 1994. He is also remembered as being involved in a sickening incident in 1997, when he physically dislocated his knee cap while laying a tackle. However he knocked it back into place immediately after and incredibly played the next week. Other notable moments in Cresswell's career include a number of game winning goals. Particularly, a kick after the siren to score a goal and secure victory for the Sydney Swans over North Melbourne Kangaroos in round 4 of the 2002 season.
Following his retirement as a player Cresswell became an assistant coach, firstly at Geelong and then at Brisbane. He then moved back to Tasmania and coached the Tasmanian Devils in the VFL. Cresswell's brother Shane had coached Ulverstone to the premiership in 2000. In 2009 Cresswell was appointed player coach of Division OneSydney 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.
