The first Highland Games to be held in Helensburgh is believed to have been held in 1898 in Larchfield Park, with Sir James Colquhoun of Luss as President. It was considered so successful that it was extended considerably in the following years.

In the 1899 Helensburgh Highland Games , Piper MacPherson of the Royal Scots & Charles McIntosh from Motherwell wrestled for most of the afternoon. Neither could put the other down, and the bout had eventually to be declared a draw.
The football place kicking competition was won by Mr Mathiew Dickie, who had been awarded his first international cap as Scotland’s goalkeeper the previous year.

The highlight of the 1900 Games was the ascent by balloon and descent by parachute of a lady parachutist, Maud Brooks.
The Balloon was released about 4pm, climbed rapidly, and vanished into the clouds. However the intrepid Miss Brooks landed a few minutes later on the West Highland railway line, near Upper Colquhoun Street.

At the 1901 Games the World Wrestling Competition was contested by Tom McInerney of England & George Ross the Scottish champion. To the disappointment of the crowd, the title went south.

At the 1902 Games, A.A. Cameron from Partick broke the world record for putting the 56lb weight, achieving 40ft 10 ins.

In 1903 the programme included tent pegging, lemon cutting, a Balaclava melee & wrestling on horseback by the Royal Field Artillery.

Unfortunately the 1905 Games made a loss, & there were no more Games until 1924, when Provost J.F. Duncan organised a’Gathering & Athletic Carnival’ at Larchfield Park, attended by over 4,000.