Cutler joined the third series of Strictly Come Dancing in 2005, when he and Siobhan Hayes left in week one. He partnered Carol Smillie in 2006, reaching week nine, and won the competition in 2007 with partner Alesha Dixon. In January/February 2008 Matthew competed with ex- Olympian Denise Lewis on the Strictly Come Dancing Tour. He partnered Christine Bleakley in the 2008 series and finished 5th overall. In January/February 2009 Matthew danced with Kristina Rihanoff on the Strictly Come Dancing Tour. For the 2009 series of Strictly Matthew partnered Tennis ace Martina Hingis. He and Martina were the first couple to leave the 2009 series. His professional partner for 2009 was one of the new girls Aliona Vilani. He did not return for the eighth series in Autumn 2010 but returned for the Christmas special, partnering Fern Britton.
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