Cadogan came through the Crystal Palace Academy[3] where he caused a stir as an effective right winger as his considerable skill and crossing ability made him a formidable opponent for full backs.

Cadogan had a particularly impressive game against Brentford the week before the championship campaign opened, scoring a goal and showing his quality against league opposition under the eyes of the new manager.

[10] Cadogan then went on to start the first game of the season for Crystal Palace making his full debut under George Burley in the 3–2 win against Leicester City, assisting Darren Ambrose's goal.

[11] On 24 August 2010, in the second round of the League Cup game away to Portsmouth where Edgar Davids made his Crystal Palace debut, Cadogan came off the bench in the 68th minute.

[12] On 2 October 2010, Cadogan scored his second senior goal for Crystal Palace in the 1–2 defeat to Queens Park Rangers, then managed by the man who had given him his professional contract, Neil Warnock.

The billboards, also featuring teammates Sean Scannell and Nathaniel Clyne, advertised the graduates born in South London who had come through the Crystal Palace academy.

[15] In the 2011–12 season, after featuring in just two games for Crystal Palace, he was loaned out to League Two side Rotherham United in January to continue his footballing education and gain experience.

[21] At the end of the 2012–13 season, when Aldershot Town were relegated from The Football League, Cadogan was one of thirteen players to be made redundant in the wake of the club's administration.

[26] On 11 August 2014, following an unsuccessful trial with Scottish Championship winners Dundee, where he started in a 2–0 victory over English champions Manchester City,[27] Cadogan signed a season-long deal with Swedish Superettan club GAIS.

[29] He made his first appearance for the club on 4 March, coming on as a 68th-minute substitute for Maxime Biamou in a 0–0 draw at Barrow, Sutton's first away clean sheet back in the non-League top flight since a 9–0 away victory against Gateshead on 22 September 1990.