It was launched in 1988 as the Kaupthing Singer and Friedlander / Sunday Times Watercolour Competition, through sponsorship by Kaupthing Bank and The Sunday Times.
Subsequent winners have included Trevor Stubley (1990),[3] Carl Randall (1998, the youngest ever 1st prize winner),[4] Stuart Pearson Wright (1999; third prize), Leslie Worth, and Carol Robertson.
In 2008, 2,000 works were submitted, with 100 exhibited at the Royal Watercolour Society's Bankside Gallery, and a £25,000 prize fund,[5] that year's winner being Jennifer McRae.
Her winning painting in 2014 was Fat Boy's Diner, which depicts a cafe near Trinity Buoy Wharf in London.
The trip inspired her winning 2016 entry, Sandy Shoes.