Milton Keynes Dons First Team Coach Paul Mitchell is riding from Lands End to John O'Groats to raise money for Help for Heroes.
Paul, who is also the Ambassador for MK Dons' Sport and Education Trust, will be joined by a number of other club staff and supporters.
The group are aiming to raise £20,000 for the Trust and Help for Heroes, which is The Football League's nominated charity partner for the 2009/10 season.
Local bicycle company Trek have supported the cause by supplying the team with custom bikes in the Dons' colours. The challenge begins on Sunday, June 6.
Help for Heroes has been high on the agenda at the League 1 club since striker Peter Leven promised to donate £5 for each goal the club scored.
Paul said: "With the support that Peter and the Football League have thrown behind the campaign, we thought we should be doing our part in the Sport and Education Trust.
"I recently lost a friend who was serving in Afghanistan and would like to see as much money raised for both charities as possible."
Football League Director of External Affairs Gavin Megaw said: "Help for Heroes is an important charity and we fully support any club or staff member doing their bit to raise funds.
"We want to say a big thank you to Paul and his colleagues at MK Dons for organising this event."
Help for Heroes co-founder Bryn Parry added "Help for Heroes thanks the team from MK Dons for their fantastic support for our wounded heroes."
To donate to the cause, please log on to www.justgiving.com/SETH4Hbikechallenge.
For all the latest news on MK Dons please click here
Help for Heroes has been selected as the official charity partner of The Football League for the duration of the 2009/10 season click here for more information