Raven captained England at various youth levels. He was promoted to Melwood in January 2004 after impressing with the reserves, but didn't make the progress expected and only featured in four games for Liverpool. He made his debut in a 1-1 draw at Tottenham on 1 December 2004 in the League Cup and started in another under-strength side in a shocking FA Cup defeat to Burnley two months later. In the following game he replaced Sami Hyypia for the last third of the League game at Southampton, which turned out to be Liverpool's third defeat in a row. His last game was another unsuccessful cup outing, this time at Selhurst Park where Palace beat Liverpool 2-1 on 25 October 2005. Raven played 11 games for Tranmere on loan in the 2005/06 season, enjoying his stay at the club for which he played at schoolboy level and supported as a kid. Raven was sold in the summer of 2006 to Carlisle United who had just been crowned champions of League Two. The right-back played over 130 League games and earned cult hero status at Carlisle but was released by the club and joined Shrewsbury Town prior to the 2010/11 season.
In the summer of 2011 Raven returned once more to Tranmere. He played in 17 League One fixtures for Tranmere during the 2011/12 season before moving to Terry Butcher's Inverness Caledonian Thistle in Scotland and has since played over 100 games for them. He scored the winning goal in the 2014/15 Scottish Cup semi final against Celtic but missed the final victory over Falkirk due to injury. In 2015-16 he was a regular until January when a foot injury ruled him out for two months and had to settle for a place on the bench when regaining fitness, but remained at the club for 2016-17. It was another injury disrupted season in which Inverness were relegated. Raven stayed with the Highlands club, but as they looked to cut the costs of higher earning players, he agreed to a contract termination in January 2018. He spent the rest of the season with Wrexham in the National League and after being released joined Warrington Town, two divisions lower and began to concentrated on securing coaching badges.
During 2018-19 Raven took up a full time coaching position at Ellesmere College and was named in the Northern Premier League's team of the year. However his side just missed out on promotion to the National League North, losing to Kings Lynn in a play off. Putting the disappointment behind him he agreed to remain at the club for the 2019-20 season. In September 2020 he joined Marine, helping them to the third round of the FA Cup where they were beaten at home by Tottenham. Due to Covid 19 curtailing the season, he ended up playing more FA Cup than Northern Premier League games.
Raven left Marine in December 2021 to become assistant manager at Warrington Town, announcing his retirement from playing at the same time. He has also developed K2 Performance, a match analysis platform for non league clubs.