Leading Sires of 2YO Winners
(through 31 December 1999)
| Rank | Stallion | State | Foals | Winners |
| 1 | TOUR D'OR | FL | 84 | 26 |
| 2 | *RIZZI | FL | 50 | 19 |
| END SWEEP | JPN | 66 | 19 | |
| 4 | *CHEROKEE RUN | KY | 55 | 17 |
| CARSON CITY | KY | 76 | 17 | |
| HADIF | TX | 50 | 17 | |
| 7 | MOUNTAIN CAT | Turkey | 72 | 16 |
| WEST BY WEST | KY | 70 | 16 | |
| 9 | DEPOSIT TICKET | PA | 67 | 15 |
| DIABLO | FL | 65 | 15 | |
| GILDED TIME | KY | 82 | 15 | |
| STORM CAT | KY | 58 | 15 | |
| 13 | BAG | LA | 50 | 14 |
| DEHERE | JPN | 86 | 14 | |
| NOTEBOOK | FL | 55 | 14 | |
| PROSPECTORS GAMBLE | KY | 60 | 14 | |
| TRICKY CREEK | CA | 49 | 14 |