The Cascade started life as the jointly promoted Squires Trophy Rally back in 1963 and was named after the clubs first chairman Len Squires. During the late 60’s and early 70’s it remained the clubs premier event, changing format from time to time to keep in line with the ever changing R.A.C. legislation.
1977 saw Cascade Motors of Dartford Donate the Cascade Cup and some sponsorship money to help promote the event, The event was promoted as novice event, with easier navigation being given to Novices and Beginners, the only other class to take part being that of the Experts.
In 1981 the works supported 848cc Reliant Kitten of Graham Newby & Brian Parker took part in the 95 mile all tarmac event humbling many crews by winning the event by 3 minutes & only dropping a minute all night.
Cascade Motors remained the main sponsor until 1982, the organisers found various sponsors in the years after but retained the name Cascade to help identify the event.
In 1987 Scott Bowater along with several others sponsored the Andrex Charity Rally for the Cascade Cup when the event raised over £2000 for the children in need appeal.
During the last decade, when road rallies in the south east of England have been as popular as smoking on a tube train, the cascade had been dropped in favour of support towards the clubs premier event The Powerush.
In an effort to help promote grass roots motor sport a decision was made in 1998 to resurrect The Cascade Cup. Primarily aimed at the Novice with the offer of trial membership, easy navigation and local lanes new members are being encouraged with to experience the buzz of competition on a series of 12 cars run over 6 weeks period with one event per fortnight. Experts can take part but are not eligible for overall awards.
| Year | Driver | Navigator |
| 1976 | Martin Holland | David Clark |
| 1977 | Barry Laver | Jamie Amis |
| 1978 | Barry Laver | Jamie Amis |
| 1979 | Rick Jarvis | Mick Baxter |
| 1980 | Richard Highams | Dave Barnes |
| 1981 | Graham Newby | Brian Parker |
| 1982 | Phil Spurge | Pete Tilling |
| 1983 | Arnie Ward | Dave Jones |
| 1984 | Mick Shotter | Pete Turner |
| 1985 | Event Not Run | |
| 1986 | Stuart Bathollomew | N. Davison |
| 1987 | Derek Arnold | S. Rush |
| 1988 | Event Not Run | |
| 1989 | Event Not Run | |
| 1990 | J. While | M. Row |
| 1991 | Mike Biss | Pete Tilling |
| 1992 | Event Not Run | |
| 1993 | Terry Schraider | Rod Boteley |
| 1994 | Terry Schraider | Chas Davies |
| 1995 | Event Not Run | |
| 1996 | Event Not Run | |
| 1997 | Event Not Run | |
| 1998 | Paul Barnes | Robert McCartney |
| 1999 |
Stuart Gibson |
Steve Gibson |