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Originally presented by Victoria Marine, the Victoria Cup is awarded annually by the Island Sailing Club to the winning Victoria Yacht, on corrected time, in The Round The Island Race. The top panel states:
ROUND THE ISLAND RACE
FIRST VICTORIA YACHT
ON HANDICAP
PRESENTED BY
VICTORIA MARINE
The trophy was first awarded in 1991, the year our Association was founded, and winners' names were engraved on individual plaques; one for each year. In 2008, it was discovered that there was no longer any space to add a further individual plaque. The trophy was also looking a little 'tired'. A decision was made to refurbish the trophy and to summarise the past winners onto two larger plaques. We are greatly indebted to Jerry Bottrill, who supervised the work and is also the author of all the photographs you see on this page.

Old style individual plaques



The refurbished cup with summary plaques
| 1991 | VICTORIA PLUM | CLAUDE FIELDING |
| 1993 | SAMPHIRE | MOWBRAY WHIFFIN |
| 1994 | OSPRAY | MELVYN LARKIN |
| 1995 | SHIKARA II | BOB HATHAWAY |
| 1996 | BLUE ALLIGATOR | A. WALLIS |
| 1997 | AMOURETTE OF HAMBLE | ALISON & HARRY THOMPSON |
| 1998 | HOTWATCH OF HAMBLE | DAVID CLEMENTI |
| 1999 | BLUEBELL OF WARSASH | C. FIELDING, R. HATHAWAY |
| 2000 | FRUSS | C. HULLAND, P. WESTON |
| 2001 | FRUSS | C. HULLAND, P. WESTON, S. AUGHEY |
| 2002 | FELICITY | R. DAWKINS, A. PRICE, B. PARKER |
| 2003 | FELICITY | R. DAWKINS, E. JENKINS, P. BAXTER |
| 2004 | SAMPHIRE | MOWBRAY WHIFFIN |
| 2005 | SAMPHIRE | MOWBRAY WHIFFIN |
| 2008 | TRACKER | JERRY BOTTRILL |