The Master's Medal came into being in 2001 when the Court gratefully accepted a proposal by Past Master Peter Gell. The proposal was that an award be made to a Liveryman for service to society (including but not necessarily for educational and charitable endeavours on behalf of the Company) and that it be made annually unless otherwise decided by the Master. Funds were provided for the first four recipients to make a £1,000 donation to a charity of their choice.
The first Medal was presented in 2001 by Master Peter Gell, to Liveryman Roy Nunn who rode his horse around the coasts of England and Wales. At the time Roy wrote: "My charity ride on horseback brought me many rewards from warm-hearted people and allowed me to raise £52,000 for several charities. The charitable endeavour also provided a purpose and an incentive for my effort when faced with the frustrations which inevitably arise in completing such a project. The Essex Air Ambulance will benefit from the £1000 from the Company's generoud donation"
In 2002, Master Keith White made the award to a Liveryman and Past Master Ian Dussek who had served on the Highway Engineering Educational Trust since 1977, initially as a trustee and then as chairman from 1986. He stepped down that year after 25 years of service. During that period over £200,000 was disbursed, a very considerable responsibility. In addition he initiated, with his father, also a Past Master, the Paviors' Lecture first given in 1975. He was responsible for the arrangements for all the lectures since then until 2002.
In 2003, Master Ivan Nellist presented the medal to Liveryman Tom Barton for his success in raising record amounts for charity in the Inter-livery Swimathon.
In 2004, Master Robin Wilson presented the medal to Honorary Assistant John Sunley to mark the Company's appreciation of the generosity it has received over the years from the Bernard Sunley Charitable Foundation. In 1983 a donation of £50,000 was made to the Company's Highways Engineering Education Trust with a further donation in 1990. In 1998, the Foundation put up £25,000 to be matched by members of the Company. John Sunley, as winner of the Medal, nominated the Kent Association for the Blind to receive his £1000 award.
In 2005, Master John Carpenter presented the medal to Robin Wilson for overseeing and progressing the Company's charity funds.
In 2006, Master David Laing presented the medal to David Marshall for his dedication as the Company's Almoner.
In 2007, Past Master David Laing presented the medal to Keith Lambert for his success in raising in excess of £40,000 for the Bobby Moore Cancer Fund by staging a celebrity Golf Day at Woburn in July 2006. Keith was also presented with a model of Temple Bar commissioned by Past Master Laing to be awarded annually to the recipient of the medal. Keith has also been a dedicated member of the Paviors swimming team raising money for the Lord Mayor's charity through the Inter-Livery Swimathon.