| Rank | Race | Moment |
| 25 | 2003 Juvenile Fillies | Julie Krone becomes the first female jockey to win a Breeders' Cup race. |
| 24 | 2006 Juvenile | Eventual Kentucky Derby champ Street Sense takes command. |
| 23 | 2003 Classic | Pleasantly Perfect gives Richard Mandella four Breeders' Cup wins on the day. |
| 22 | 1990 Sprint | Dayjur jumps a shadow and Safely Kept wins. |
| 21 | 1985 Turf | Pebbles defeats a stellar field of male rivals. |
| 20 | 1993 Mile | Lure circles the field to a second consecutive Mile victory. |
| 19 | 2002 Juvenile Fillies | Storm Flag Flying fights back to win. |
| 18 | 1998 Classic | Awesome Again upsets the Classic to complete an undefeated season. |
| 17 | 1988 Mile | Miesque becomes first two-time Breeders' Cup winner. |
| 16 | 2002 Distaff | Azeri wins in a Horse of the Year performance. |
| 15 | 1994 Juvenile Fillies | Serena's Song and Flanders battle to the finish. |
| 14 | 1993 Classic | Arcangues stuns the world at odds of 133-1. |
| 13 | 2003 Turf | The first ever Breeders' Cup dead-heat. |
| 12 | 2006 Filly and Mare Turf | Ouija Board wins her second Breeders' Cup Filly & Mare Turf. |
| 11 | 1988 Classic | Alysheba wins the "Midnight Classic." |
| 10 | 2007 Classic | Curlin dominates an all-star field. |
| 9 | 1998 Mile | Da Hoss wins his second Mile after two year absence. |
| 8 | 1984 Classic | Wild Again prevails over Slew o' Gold and Gate Dancer. |
| 7 | 1986 Distaff | Lady's Secret leads all the way in a Horse of the Year performance. |
| 6 | 1991 Juvenile | Arazi runs away with the Juvenile. |
| 5 | 1989 Classic | Sunday Silence defeats Easy Goer for Horse of the Year. |
| 4 | 1987 Classic | Derby winners Ferdinand and Alysheba hit the wire together. |
| 3 | 1995 Classic | Cigar completes an undefeated season in the Breeders' Cup Classic. |
| 2 | 2001 Classic | Tiznow wins second consecutive Breeders' Cup Classic. |
| 1 | 1988 Distaff | Personal Ensign completes an unbeaten career in dramatic fashion. |
