
| May 19, 1964 | First win, at Presidente Remon racetrack, Panama |
| 1970 | Won George Woolf Memorial Jockey Award |
| 1971 | First Eclipse Award |
| 1973 | Second Eclipse Award |
| 1974 | Third Eclipse Award |
| July 17, 1975 | 3,000th win |
| 1975 | Inducted into the Hall of Fame |
| 1979 | Fourth Eclipse Award |
| September 30, 1981 | 5,000 win aboard Wander |
| May 5, 1984 | Kentucky Derby win on Swale |
| February 17, 1985 | 6,000th win |
| 1985 | Won Big Sport of Turfdom Award |
| 1985 | Fifth Eclipse Award |
| March 14, 1987 | Won 7 races in one day at Santa Anita Park |
| November 9, 1988 | 7,000th win |
| May 28, 1990 | $150 million in total earnings |
| January 28, 1991 | 7,500th win |
| June 17, 1992 | Became Hollywood Park's winningest rider of all time |
| August 29, 1993 | 8,000th win |
| December 1996 | Received the Mike Venezia Memorial Award |
| January 1, 1997 | 8,500th win |
| September 2, 1998 | Became Del Mar's winningest rider of all time, aboard Lady Cadet |
If anyone knows the dates of his other major accomplishments, such as 1,000th win, 2,000th, 4,000th, and 5,000th, please email me at rvotaw@selu.edu and let me know. Thanks!