Matt Flynn initially joined Dale on a one month loan deal from Macclesfield in August 2009, but towards the end of that month he put pen to paper on a two year deal, keeping him here until the summer of 2011.

Matt started his career as an apprentice at Macclesfield and earned himself a professional contract in the summer of 2007. He impressed enough for The Silkmen to extend this until the end of the 2007/08 season, before they offered him another one year deal to keep him at Moss Rose until the summer of 2009.

Matt made 31 appearances in the 2008/09 season for Macclesfield, showing enough promise for Keith Alexander to give him another one year deal in the summer. However, after not catching the first team at Moss Rose, Keith Hill moved quick to loan in the 20 year-old towards the start of the season. Matt impressed the Dale fans and Hill alike in his first few games and signed permanently for Dale on the 27^th of August.