Career
Cummings started his career at Chelsea but never made it into the first team, and instead was loaned out several times – Bournemouth 2000-2001, West Bromwich Albion 2000-2001 and 2001-2002, and Dundee United in 2002-2003. Following his return from the Dundee United loan spell, Cummings was again loaned to Bournemouth, for a three-month spell, before signing a permanent deal with the club In the following season he established himself as a first team player, making 46 appearances in total and scoring 2 goals.
The 2004-2005 season brought a playoff push for "The Cherries", with Cummings playing an important part and scoring 3 goals.
However, during an away derby with Swindon Town in March 2005, he suffered a double broken leg in a crunch tackle by Swindon"s Steve Jenkins. This was a major blow to both Cummings and Bournemouth, and was a major factor in them failing in their playoff bid.
Nonetheless, Cummings signed a new deal with Bournemouth in the summer of 2006. He made his league return as a late substitute in the 3–0 defeat to Chesterfield at the start of the 2006-2007 campaign.
In June 2007 Cummings signed a new two-year deal with Bournemouth.
He broke his arm in a 1–1 draw with Northampton Town on 15 September 2007. On 29 June 2012 it was announced that he has signed with League Two club AFC Wimbledon. He played a total of 9 league games for the "Dons" before being released from the club on 10 July 2013. on 16 August 2013, Cummings joined Southern League Premier Division side Poole Town.
