Norwich City signed Peterborough's England Under-21 international central defender Ryan Bennett at the close of the January 2012 transfer window for a sum reported to be £3.2m. He was immediately loaned back to ther Posh to give them some time to recruit another defender on loan. Club Manager Paul Lambert said of the transfer: “I’m delighted we have signed Ryan. He’s made a bright start to his career at Grimsby and Peterborough; he’s an England U21 international and he’s got so much potential."Supposedly Bennett was on his way to have a medical ahead of a move to Swansea when he received the Norwich enquiry and he turned around and headed to Norwich.

A product of Ipswich's youth team, he was released from Portman Road at the age of 16. He joined Grimsby and quickly broke into their first team. Bennett made his professional debut as an 88th minute substitute, replacing Danny Boshell in a 2–1 win over Milton Keynes Dons in April 2007. 21 days later he became the club's youngest ever captain, aged only 17 years old when Grimsby's all time record appearance holder John McDermott passed him the skippers armband after being substituted in the local derby with Lincoln City. With the appointment of Mike Newell as first team manager in October 2008, Bennett was handed the captain's arm-band for the remainder of the 2008–2009 campaign aged only 18

After 103 league appearances, he signed for Peterborough United on 23rd October 2009 on an initial three-month loan deal with a view to a permanent move. Bennett made his loan at London Road permanent on 23rd January 2010, signing a four-and-a-half-year contract, with Grimsby reportedly receiving £500,000, possibly rising to £1 million

Bennett was called up for the England under-18 side that faced Austria on 16th April 2008. It was his first England call-up. He played the full game in the 2–0 victory. On the 29th September 2011 Stuart Pearce gave him his first call-up to the England U21 after he impressed him in the home win against Burnley. On the 10th of October Bennett made his international under 21 debut in the 2–1 win away against Norway's Under-21s.

Ryan made his Norwich debut on 30th March 2012 in the 2-1 defeat at Fulham. He ended the season with eight appearances. He made 20 appearances the following season, scoring his first Norwich goal in the 2-1 win over Reading.

Bennett made 20 appearances, scoring once in the 2013/14 season in which Norwich were relegated from the Premier League.

An injury against Ipswich at the end of Augsut 2015 saw Bennett limited to eight appearances for City in their Championship play-off winning season.

Bennett made 24 appearances for City in 2015/16, as the Canaries were relegated from the Premier League.

On 9th June 2016, Ryan was the subject of media speculation linking him witha move to Premier League newboys Middlesbrough. Hull and Celtic were also said to be interested. I January 2017, Notts Forest were said to be keen to sign Bennett but Alex Neil was keen for Bennett to be competing for a first team place at Carrow Road.

On 2nd May 2017, Norwich City announced that they would not be renewing the contracts of seven senior players in the summer including Bennett. He had made 37 appearances during 2016/17. He was quickly linked with Brighton and Birmingham. He spoke with Sheffield United before he signed a three year contract with Wolves on 31st May 2017.

Bennett established himself as a regular in the Wolves defence as they won promotion back to the Premier League in 2017/18 and secured the Championship title. He then made 40 appearances the following season. In 2019/20 he had made 19 appearances, including games in the Europa League but was allowed to join Leicester City on loan on 31st January 2020, with an option to make the move permanent in the summer of 2020. The Foxes had needed to strengthen their options in central defence and Bennett's arrival allowed them to loan Croatian centre-back Filip Benkovic to Bristol City.

Following reports that Daniel Farke was looking to add some experienced players to his City squad in August 2020, one name that was suggested was former Norwich defender Ryan Bennett who still has a home in Norfolk.Now in his final year of his contract with Wolves, he has slipped down the pecking order but Wolves reportedly have asked for £3million for his signature.

On 29th September 2020 it was reported by the Press Association's Nick Mashiter that Fulham would be turning to a loan deal for Bennett following the failure of their interest in Ben Godfrey to materialise into anything substantial. Bennett signed for Swansea City on a free transfer on 16th October 2020 although the deal features clauses which are likely to see Swansea pay a fee should Bennett help them win promotion to the Premier League. He was one of four incomings to Swansea alongside midfielder Kasey Palmer from Bristol City, utility player Ryan Manning from QPR and Manchester City youngster Joel Latibeaudiere whilst Swansea centre-back Joe Rodon joined Spurs for £11million.

He left Swansea on 1st September 2022 by mutual agreement. He had played 47 times for the Swans.

On 6th January 2023 he signed for Cambridge United on a contract until the end of the 2022/23 season. He then signed a new one year contract on 3rd July 2023 having made 21 appearances for Cambridge in his first half-season.

He was released by Cambridge on 1st May 2024 having made 64 appearances, scoring once (against Carlisle)

Bennett announced his retirement on 14th October 2024. "I'm done with playing. I knew four months before the end of last season. That decision was made. Nobody believed me when I was telling them I was done. People said it was a silly decision, but it is what it is. I'm not one for formal announcements, so I sailed off after the final game, and that was it." He said that there had been enquiries during the Summer of 2024 from clubs but that his aspiration was to become a sporting director. "I've been spending time with the PFA and the business school there to look at being accredited with a sporting directorship. I've been doing some talent ID work for the last year and a half, two years. It keeps you busy. I'm looking to do some work with data to understand a little bit more about that and how to utilise it in different ways to see where I go. My end goal is to be the sporting director. That is what I want to do. I've spoken to people and had interviews with clubs. I know the game tactically from my years in it, and I have a good network from when I played, but the question was always, 'How well do you understand data?'. I'd been exposed to it in presentations and understanding little bits here and there about how an opposition might want to play, but it was clear I needed to add that string to my bow. The data and working side, I am a novice. I'm not naive enough to know that I'm a first-year apprentice in the working world. There are people out there with five, six, or more years of experience working in football who don't have the playing side, so I need to catch up a little bit. I don't agree with being fully data-driven. Data is a great tool that can enhance you in areas and prove your eye or findings, highlighting patterns or people in certain metrics you're looking for. I am a novice in that, and there are bits I haven't been exposed to. But I'm willing to learn those bits to get me to the next level."

"My interest first started when I was at Swansea. It was during Covid, so I spent a lot of time by myself locked in a house, thinking about what I was going to do. I probably realised a bit late and I wish that I'd thought about it sooner. The easy option was 'ah, I'll just be an agent', but the older that I got, the less it appealed to me," he said.