Although the early records of the Society are unfortunately no longer available, legend has it among the descendants of the founders, that an informal challenge match was arranged in 1894 following an argument in either the Rose and Crown or Saracen's Head by several at the local farmers as to their respective capabilities as ploughmen. Joseph Harrison, it is thought, may well have been the prime organiser of the first competition proper in 1895.
The match was held on 13th November 1895 at Mr. H. Yates's farm in Brailsford. Each year the Match continued to grow and more classes were added. In 1910, the first set of formal rules to govern the Society were drawn.
By the time the 1914 Match was due to be held, war had already been declared and the decision was taken to cancel the Match. In 1919 thought was given to winding up the Society but activities resumed again in 1920 and the matches began again in 1921.
A Tractor ploughing class was incorporated into the schedule for the first time in 1922 but this was subsequently dropped in 1925 after poor support.
The first social evening arranged by the Society was a "hot supper" which took place at the Rose & Crown in March 1926. The following year saw the first school visit by the children of Brailsford School.
The Matches continued until 1939, when that year's Match had to be cancelled due to the outbreak of the Second World War. The matches resumed again in 1944.
By the time the 1950s arrived, the Society was continuing to grow in stature. Membership was growing and the finances were in good shape. In 1950, there were 5 tractor ploughing classes in the schedule.
In 1952, the Society affiliated to the newly formed British National Ploughing Association (now called the Society of Ploughman) and in 1953, the Society sent two competitors to the first National Competition, held in Lancashire.
1962 saw a major change in the structure of the Society, when the Ladies Section was formed.
The early 1970s also saw the introduction of classes where samples of wheat and barley were judged on all round quality. In 1974/75 the Society introduced hedgecutting training which still continues today
Another new feature in the Spring of 1975 was a Ploughman's Night - held at Brailsford Village Hall.
Three other produce classes were introduced at the 1978 Match, which were classes for the best bales of hay and barley straw and a silage making competition, judged in situ on the farm.
In the early 1980s, the Dance Committee which had existed for some 50 years ceased it activities as a separate body and was amalgamated into the main Society. In the 1980s and 1990s, the Society held an Annual Clay Pigeon Shoot, which became popular with non-members but was later dropped when interest waned.
Following requests from interested parties for a competition for Stick Makers and Dressers, a committee was formed in the 1990s to organise this. This competition proved to be very popular and remains so today.
The Centenary of the Society saw the 90th Match. It was agreed that year to revive the religious ceremony of Plough Sunday. For the Centenary, the committee also held a social event at The Grange, Barrow-on-Trent.
The 100th Match was held in 2005 at Covert Farm, Church Broughton.
A full history of the Society can be found in the publications "The Long Furrow" by Lance Waud and "Ploughing On" compiled by J. Derek Evans, MBE, both of which are available from the Society.