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After suffering a series injury his Eastleigh contract was terminated by mutual consent in December 2018. In 2019 he had a trial for York City for 3 weeks but wasn't signed permanently and chose to sign for Mickleover Sports. He joined Boston United on 22 March 2019 making his debut a day later.

On 12 July 2019, Cresswell joined Bradford (Park Avenue). After playing six games, he left the club and joined Romford F.C. on 19 November 2019. He left Romford in January 2020.

In August 2016 Cresswell joined National League club Eastleigh.

On 1 September 2014, Cresswell signed for Northampton Town for an undisclosed fee on a three-year contract. He made his debut for the club against Dagenham & Redbridge. He scored his first goal for the club in a 1–1 draw against Wycombe Wanderers with a header from Joel Byrom's cross in the 31st minute. He was voted the club's Player of the month for November 2014. In January 2015, Southend manager Phil Brown revealed that he wanted to resign Cresswell in the summer transfer window, but the financial strains of the club prevented him from doing so.

On 23 July 2013, Cresswell joined Fleetwood Town on a two-year contract for an undisclosed fee, with Southend manager Phil Brown stating that the reasoning was that Cresswell wanted to return to Northern England. On the opening game of the season, he scored a 56th-minute goal in a 3–1 victory against Dagenham & Redbridge. He ended the first season with Fleetwood, making 26 appearances in all competitions, as Fleetwood won promotion into League One.

Cresswell again changed clubs in 2012, penning a contract for Southend United. He was named in the League Two PFA Team of the Year for the 2012–13 season. The following season, he was transferred to Fleetwood Town with whom, he won promotion to League One. In 2014, after failing to make much impact at Fleetwood he again came to League Two, joining Northampton Town

On 3 July 2012, Cresswell signed for League Two club Southend United on a two-year contract, after Rotherham allowed him to talk to other clubs. On 25 August 2012, Cresswell scored his first goal for Southend, a 92-minute equaliser in a 3–3 draw with Northampton Town. On 4 September 2012 Cresswell scored another injury time goal, this time it proved to be the winner as Southend triumphed 2–1 over AFC Wimbledon in the first round of the Football League Trophy.

Creswell, along with teammate Sean Clohessy, was named in the League Two PFA Team of the Year for 2012–13.

In June 2010, Cresswell joined Rotherham United on a three-year deal for an undisclosed fee. He scored on his debut, finding the net in the 88th minute against Lincoln City He again found the net, in a high scoring match of 10 goals against Cheltenham Town, helping the team to overturn a three-one deficit. He ended the first season with Rotherham scoring 5 goals in 26 matches, getting 3 yellow cards.

A graduate of the Sheffield United youth academy, Cresswell failed to break in the first team and was hence loaned to clubs in the lower divisions of English football. In 2008, after being released by Sheffield United, he signed for Bury in League Two. Playing more than 50 matches for the club, he joined Rotherham United two seasons later.

He joined Macclesfield Town on loan for the remainder of the season in January 2008 where he played 19 times, scoring one goal.

Despite joining up with Ferencváros for pre-season training only a few weeks after agreeing the loan move Cresswell joined Bury on 2008. He made his Bury debut as late substitute in the first game of the season in a 1–0 win at home to Brentford on 9 August 2008. Cresswell got his first goal for Bury on 1 November in a 1–0 win at Notts County. He was red carded in the last match of the season against Chester City. In the second season with the club Cresswell made 31 appearances, scoring in none.

Cresswell went out on loan again at the start of the 2007–08 season, spending time at Rotherham United. Sheffield United recalled him however because they did not think he was playing enough games having started only two games for the Millers, and making two substitute appearances. He was quickly loaned out again, this time to Morecambe but only managed a further two league appearances at Christie Park.

Cresswell was born in Rotherham, South Yorkshire. He started his career with Sheffield United, with whom he signed his first professional contract in July 2006. He got his first taste of first-team football with non-league Halifax Town where he was loaned during the 2006–07 season.

Ryan Anthony Cresswell (born 22 December 1987) is an English professional footballer who plays as a centre back for Parkgate FC.