| Year | Winner | State Bred | Listed in order of most recent win by that location. (KY last year, TX longest without a win) | |||
| 2001 | MONARCHOS | KY | ||||
| 2000 | FUSAICHI PEGASUS | KY | ||||
| 1999 | CHARISMATIC | KY | Location | Wins | % since 1950 | |
| 1998 | REAL QUIET | KY | KY | 33 | 63% | |
| 1997 | SILVER CHARM | FL | FL | 6 | 12% | |
| 1996 | GRINDSTONE | KY | VA | 3 | 6% | |
| 1995 | THUNDER GULCH | KY | PA | 1 | 2% | |
| 1994 | GO FOR GIN (sly) | KY | CAN | 2 | 4% | |
| 1993 | SEA HERO | VA | IL | 1 | 2% | |
| 1992 | LIL E. TEE | PA | MD | 2 | 4% | |
| 1991 | STRIKE THE GOLD | KY | CA | 2 | 4% | |
| 1990 | UNBRIDLED (gd) | FL | ENG | 1 | 2% | |
| 1989 | SUNDAY SILENCE (my) | KY | TX | 1 | 2% | |
| 1988 | WINNING COLORS | KY | ||||
| 1987 | ALYSHEBA | KY | ||||
| 1986 | FERDINAND | KY | ||||
| 1985 | SPEND A BUCK | KY | ||||
| 1984 | SWALE | KY | ||||
| 1983 | SUNNY'S HALO | CAN | ||||
| 1982 | GATO DEL SOL | KY | ||||
| 1981 | PLEASANT COLONY | VA | ||||
| 1980 | GENUINE RISK | KY | ||||
| 1979 | SPECTACULAR BID | KY | ||||
| 1978 | AFFIRMED | FL | ||||
| 1977 | SEATTLE SLEW | KY | ||||
| 1976 | BOLD FORBES | KY | ||||
| 1975 | FOOLISH PLEASURE | FL | ||||
| 1974 | CANNONADE | KY | ||||
| 1973 | SECERTARIAT | VA | ||||
| 1972 | RIVA RIDGE | KY | ||||
| 1971 | CANONERO II | KY | ||||
| 1970 | DUST COMMANDER (gd) | IL | ||||
| 1969 | MAJESTIC PRINCE | KY | ||||
| 1968 | FORWARD PASS | MD | ||||
| 1967 | PROUD CLARION | KY | ||||
| 1966 | KUAI KING | MD | ||||
| 1965 | LUCKY DEBONAIR | KY | ||||
| 1964 | NORTHERN DANCER | CAN | ||||
| 1963 | CHATEAUGAY | KY | ||||
| 1962 | DECIDEDLY | CA | ||||
| 1961 | CARRY BACK (gd) | FL | ||||
| 1960 | VENETIAN WAY (gd) | KY | ||||
| 1959 | TOMY LEE | ENG | ||||
| 1958 | TIM TAM (my) | KY | ||||
| 1957 | IRON LIEGE | KY | ||||
| 1956 | NEEDLES | FL | ||||
| 1955 | SWAPS | CA | ||||
| 1954 | DETERMINE | KY | ||||
| 1953 | DARK STAR | KY | ||||
| 1952 | HILL GAIL | KY | ||||
| 1951 | COUNT TURF | KY | ||||
| 1950 | MIDDLEGROUND | TX | ||||