Bob Robins Cup Winners - 1958/59 to 1999/00
| Date | Winners | Score | Runners Up | Score |
| 1958/59 | Guildford Cons B | Merrow B | ||
| 1959/60 | Guildford Police | Shere | ||
| 1960/61 | Stoughton C | Guildford RBL A | ||
| 1961/62 | Ewhurst A | Shalford Serv | ||
| 1962/63 | Dennis A | Angel Hotel B | ||
| 1963/64 | Woodbridge Hill A | Guildford RBL A | ||
| 1964/65 | Guildford Police | Wonersh A | ||
| 1965/66 | Knaphill A | Normandy H | ||
| 1966/67 | Guildford Cons B | Dennis A | ||
| 1967/68 | Guildford Cons B | Shalford Vill A | ||
| 1968/69 | Brookwood A | Godalming Cons B | ||
| 1969/70 | Ockford D | Shalford Vill B | ||
| 1970/71 | Stoughton & West B | Guildford RBL D | ||
| 1971/72 | Woking Ex Serv C | Shalford Vill C | ||
| 1972/73 | Woodbridge Hill D | Old Woking E | ||
| 1973/74 | Woking Cons A | Woking Liberal A | ||
| 1974/75 | Woking Cons A | Guildford Post A | ||
| 1975/76 | Woking Cons A | Woking Liberal A | ||
| 1976/77 | Guildford Police A | Farncombe Prg C | ||
| 1977/78 | Cranleigh RBL B | Woking Liberal A | ||
| 1978/79 | Lion Sports E | Cranleigh RBL B | ||
| 1979/80 | Guildofrd Post A | Stoughton C | ||
| 1980/81 | Normandy C | Woodbridge Hill H | ||
| 1981/82 | Shalford Vill B | Cranleigh RBL C | ||
| 1982/83 | Normandy C | Bramley | ||
| 1983/84 | Normandy E | Godalming RBL B | ||
| 1984/85 | Bramley A | Dennis A | ||
| 1985/86 | Shere D | Shalford Vill D | ||
| 1986/87 | Knaphill D | Ewhurst B | ||
| 1987/88 | City C | Millmead A | ||
| 1988/89 | Knaphill D | City E | ||
| 1989/90 | Farncombe Soc B | Shalford Vill D | ||
| 1990/91 | Shalford Vill D | 3 | Ewhurst A | 1 |
| 1991/92 | City D | Brookwood Hsp D | ||
| 1992/93 | Stoughton & Westborough B | 3 | Farncombe Soc B | 2 |
| 1993/94 | Woking Ex Serv B | Gomshall B | ||
| 1994/95 | Ripley RBL B | 3 | Ritz C | 2 |
| 1995/96 | Woking Ex Serv | 4 | Merrow D | 0 |
| 1996/97 | Colours D | 3 | Old Woking B | 2 |
| 1997/98 | Knaphill C | 3 | Merrow D | |
| 1998/99 | City B | 3 | West End C | 2 |
| 1999/2000 | Knaphill D | 4 | Bramley A | 0 |