[7] 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.

[citation needed] In the summer of 2007 Bennett had re-established himself as one of the club's favoured centre backs, and in this he was handed the number 5 shirt for the coming season.

[citation needed] With the appointment of Mike Newell as first team manager in October 2008, Bennett was handed the captain's armband for the remainder of the 2008–2009 campaign aged only 18.

[11] A week later Bennett confirmed he would be staying with Grimsby for the unforeseeable future by signing a new four-year deal to keep him at Blundell Park until the end of the 2012–13 season.

[13] Grimsby chairman John Fenty had a change of heart, and following a slow start to the season for his club, he decided to cash in on the Town skipper only days after sacking manager Mike Newell.

Posh manager Darren Ferguson said of the transfer: "Ryan is an excellent signing for us, he has potential and fits in with our policy of bringing good, young players to the football club".

[13] Bennett made his loan at London Road permanent on 23 January 2010, signing a four-and-a-half-year contract, with Grimsby reportedly receiving £500,000, possibly rising to £1 million.

Bennett was expected to sign for Swansea City and had begun the drive down to the Liberty Stadium only to be rung up and told to head for Norwich when the deal fell through.

[22] Bennett scored his first goal of the 2013–14 season in a crucial home game against Hull City, where his 87th-minute header gave struggling Norwich a 1–0 victory.

[23] The goal eased pressure on manager Chris Hughton, who had recently been under-fire for a string of constant poor performances dating back to early 2013.

[28] On 19 January 2019, Bennett scored his debut Premier League goal for Wolves, a header from a João Moutinho corner, in a 4–3 victory over Leicester City at Molineux.

[30] On 7 April 2019, Bennett made his debut appearance in an FA Cup semi-final (as a second-half substitute), as Wolves lost 2–3 to Watford at Wembley after extra time.

[31] On 25 July 2019, Bennett made his debut appearance in UEFA European competition, playing the full 90 minutes of Wolves's Europa League Qualifying Second Round First Leg match against Crusaders of Northern Ireland.

[42] Amid speculation of a return to Grimsby Town following news that he had recently taken up residence in the local area, a transfer never materialised and on 3 July, Cambridge announced they had reached an agreement for Bennett to sign a new one-year deal.