Cupar Golf Club is considered to be the oldest 9 hole golf club in the country, being instituted on 7th November 1855. The original course was on private property at Tailabout Farm, where the tenant had given members permission to "exercise" twice a week. This course was laid out by the celebrated Alan Robertson of St Andrews
Sir James Low of Kilmaron opens the Clubhouse on Saturday 21st December 1907.

The Clubhouse, first opened on 21st December 1907 has been modernised and extended. The facade remains in its original state.There are good basic amenities available to non-members. The lounge overlooking the last green provides excellent meals, bar snacks and beverages to members, guests, societies and visitors

The club played at Tailabout for 21 years, but then failed to come to terms with the tenant. For a short time they played over a rather primative course at Springfield House (now Kinloss), a mile west of Cupar. new course opened at Annsmuir by Ladybank and the remnants of the Cupar club migrated there, but still preserving their identity. As Annsmuir became more attractive, the number of Cupar golfers began to increase. The golfing "boom" of the 1890's prompted members to acquire a course nearer to home.

It is natural that a club with such a lengthy history should possess many valuable trophies.Robert Richardson Esquire of Restalrig House presented one of the most cherished trophies to the club in 1864, the Victoria Medal for Autumn Competition (scratch).
Colonel Hutchison of Fife Militia (the Clubs captain in 1855) gifted the Hutchison Medal in 1856. At this time the course was only 6 holes, so competitors had to play 3 rounds. The Peripatetic Cup, dating back to the last century, is on display in the St Andrews Golf MuseumMany famous names have graced the scrolls of this club. Bob Peattie was Midlands Champion in 1923 and British Boys Champion in 1924. Charlie Todd won the Victory Cup and Duke of York Cup in the Eden Tournament. Bobby Reid (ex Chairman of British Rail) was the one-armed champion of Britain in 1954.

Below are some of Cupars more noteworthy champions:

Andrew Downie - Club Champion of Cupar and St Andrews Eden Tournament 1953
'Bob' Peattie - Midlands Champion 1923; Open Internatinal Boys Champion 1924 and 1925; Eden Tournament
J Burns - 30 years as Club Secretary
J.P. Coulter - Club Champion 1941 and 1953/54
'Bobby' Reid - One -armed Champion 1954
J.W. Gladstone - Borders Champion 1939
W.A. Anderson - Club Champion 1946, 1947 and 1948
C.M. Todd - Winner of the Vicotry and Duke of York cups at the Eden Tournament 1951
 

In later years members have donated additional trophies and a vast array of silverware now exists to cater for the very competitive nature of the clubs members