Londoner Darren Kenton played in the successful youth side of 1996/97 on either side of the defence. He progressed into the first team and made his debut in October 1997 against Tranmere. He made another 10 appearances during the 1997/98 season and made himself a regular under Bruce Rioch.

Darren was transfer-listed in mid-August 1999 but came off the list in December 1999 signing a one year extension to his contract. Supposedly Rioch gave him an ultimatum in signing the contract on offer or forgetting it. Kenton's hopes of a big money move elsewhere had diminished when he was playing well whilst transfer-listed yet had no clubs approach him. He had an excellent 2000/01 season especially under new manager Nigel Worthington. In January 2001, Darren signed another new contract that would keep him at Norwich until 2003. A second strong season followed as he helped the Canaries to the Division One playoff final in 2001/02

In October 2002, media speculation linked Kenton with a move to the Premiership. As Newcastle boss Bobby Robson continues to look for ways to plug his leaky defence, Norwich have denied the St James's Park club had made an enquiry for Kenton. The Canaries say it is all speculation, although admit interest in the 24 year-old from the 'bigger' clubs is inevitable, with Norwich having only conceded eight goals all season.A club spokesman said: "We've heard about the speculation in a national newspaper but I think at this stage that's exactly what it is. We are one of the leading Division One clubs and, with the transfer window approaching, we're going to see more of newspapers putting two and two together and getting five.Darren is one of the best defenders in the Nationwide League and I think this will be the first of maybe four or five clubs who will be linked with him. But we've had no approach from Newcastle.''

When the January 2003 transfer window opened, a number of Premiership clubs including Newcastle, Birmingham and Southampton were all linked with Kenton, who missed the clash with Grimsby on 28th December 2002 allegedly to preserve his fitness for the shop window ! The link with the South Coast grew during the first two weeks of January 2003 with many media sources claiming that Southampton manager Gordon Strachan would swoop for Kenton if he cannot secure the signing of Derby defender Danny Higginbotham. However Arsenal, West Bromwich Albion and Manchester City have also been added to the list of admirers.

Although no move was made during the transfer window, Kenton was still linked with a move to the Premiership. Football-Rumours.com reported in March 2003 that Everton were looking to sign Kenton to replace their star defender Joseph Yobo who was almost certainly going to exit Goodison in the summer of 2003.

Kenton failed to agree a new contract with the club following their inability to reach the Premiership or play-offs at the end of the 2002/03. He expressed his desire to leave. Norwich agreed to terminate his contract on 2nd May 2003 rather than the contracted date of June 31st. This would allow Darren to sign for a new club on a Bosman deal (Southampton are expected to sign him) whilst Norwich save on almost 2 months wages. Darren had made 175 appearances for Norwich, 19 as substitute, and had scored 9 goals. He finally signed for the Saints in mid May 2003.

After a season plagued with injury, Kenton finally came good with some Man of the Match performances at the end of the 2003/4 season. However it was claimed that new Saints manager Paul Sturrock would be willing to let him go with Crystal Palace manager Iain Dowie ready to swoop according to The People on 13th June 2004.

On 3rd March 2005, Darren was loaned to Leicester City. He has since returned to Southampton but has suffered from mumps. At the beginning of May 2006, Southampton announced that they would not be offering Kenton a new contract and so he was seeking a new club. That new club was Leicester with whom Darren signed a two year contract on 27th June 2006.

Darren joined Leeds United on loan on 10th January 2008. This became a permanent transfer on 31st January 2008 until the end of the 2007/8 season when Darren was released.

On 18th August 2008, Darren joined Bristol City on trial and played for them in a reserves match against Forest Green Rovers. City lost 4-2, and it was reported that neither Kenton nor fellow triallist Nicholas Alexander did enough to earn an extended stay at the club. The following month saw Darren join Cheltenham on loan and on 23rd September 2008 he played for their reserves in a 4-1 defeat to Bournemouth's second string which featured Trevor Benjamin on trial.

Kenton signed a three month deal with Cheltenham on 3rd October 2008 and made his debut the following day in a 3-3 draw at Brighton. He scored his first goal for the Robins the following week in a 4-3 win over Colchester. Kenton was expected to sign a longer term contract with The Robins in January 2009 but quit the club with manager Martin Allen understanding that Kenton had signed for another team.

Kenton then surfaced on the other side of the Atlantic trialling for Canadian side Toronto FC in a friendly against the Chicago Fire. Toronto, who play in the Major League Soccer, include former Canaries Jim Brennan and Carl Robinson in their squad.

In April 2009, Kenton signed for the Rochester Rhinos who play in the second tier of football in the USA. Kenton's deal is for one year and is subject to USL and USSF approval.

Kenton has since retired and returned to London as a male model. He returned to football coaching at non-league barkingside before rejoining Norwich in September 2016 to coach the Under-12s before progressing to the Under-13s in 2017/18.