The Cupar Road Race was first held in 1973 and was won by Stuart Easton of St Andrews University. The route started and finished at Cupar Haugh and consisted of a loop up past the Hospital to Foodieash, turning at Kedlock Feus and on to Newcarnie and returning by Carnie Lodge to the Haugh.
At some time in the 1970s the route was changed to start in St Mary's Road just east of the A913 to Perth. It was run westwards to about 400m short of Easter Fernie turning south uphill to the A91 and returning to the starting point along the A91 and A913. As the traffic through Cupar increased the finishing point was moved to outside Elmwood College. Eventually the A91 route became too dangerous and the route was changed to an out and back course on St Mary's road. According to Alan McLeod's diary the race ran this route in 1987.
Throughout this period the race was called the Cupar 6 but was known to be short and indeed the initial out and back course on St Mary's Road, when accurately measured, was found to be 5.7 miles.
During the 1980s and 1990s the race became a favourite warm up race for the London marathon and two winners of that event, Allister Hutton and Liz McColgan, ran regularly. Indeed the concern was that Liz might be running at world record pace on the course and it would never be known. This led to the decision to have an accurately measured course. Norrie Williamson, an IAAF International course measurer, tried to lay out a 10K course on St Mary’s road but it could not be fitted in before the junction of the A92 and furthermore became hilly at that point. It was therefore decided to have an accurate 5 mile (8K) course which is the one we run today.
In 2011 the race was mistakenly turned about 90m short which is unfortunate since there were a number of outstanding performances on the day. The route was re–measured in 2011 by Alan Young and differed from Norrie Williamson's measurement by being about 35m shorter each way. The new measured course was run in 2012.
Although the race was taken over by Fife AC on its formation in 1975, the early results have been lost. In 1998, when the race changed to an accurate 5 miler, the results were done electronically and all the remaining years survive.
In 2002 Ken Herriot set a wheelchair record for the course of 23.11 but sadly the road has deteriorated and is not really suitable for wheelchairs. Knowing this Mark Telford from Perth took on the course and broke the wheelchair record with 21.39.4 in 2012.
The race was not run in 2001 due to the outbreak of foot and mouth disease.