Kirkley & Pakefield striker Ryan Crisp joined Ipswich on trial in November 2011 after the 18-year-old scored four goals for the Ridgeons League Premier Division side in a 5-2 victory over Hadleigh United. It was reported by the Ipswich website TWTD that Crisp has spent time with Norwich whilst at school before joining Kirkley. Crisp joined Ipswich on a six week trial.

Early on in the 2012/13 season, Crisp joined West Brom on trial.

In December 2012, Kirkley rejected a bid for Crisp from Leiston, with manager Paul Tong revealing that several Football League clubs were interested in Crisp. Crisp then played in a reserve team game for Dagenham & Redbridge in December 2012 and agreed to join the Daggers for a longer trial in early 2013. “I took Ryan down to play for Dagenham & Redbridge Reserves in the week and he acquitted himself well,” said manager Paul Tong "He didn’t score but he did himself justice – John Still spoke to him at half-time and he wants to have another look at him. They have invited him up in the new year for a week’s trial and hopefully he can impress them again.”

He moved to Needham Market before joining Dereham at the end of May 2015

Ryan left Dereham at the end of September 2020 unable to commit to the level of football in a demanding league. In early October 2020 he signed for Harleston Town of the Anglian Combination Premier Division