Six of the most closely contested Kentucky Derbys occurred before 1900. A neck, or less victory has been accomplished 25 times in the first 136 runnings of the Run for the Roses at Churchill Downs the first Saturday in May.
Three trainer-owners of the early years of Thoroughbred racing, J.C. Cahn, John E. Madden, and T.C. McDowell, all won the Kentucky Derby as three of the 25 finishes won by a neck, or less.
Typhoon II's Upset in 1897
Six Thoroughbreds lined up for the 1897 Kentucky Derby. Favored to win was Ornament, ridden by Alonzo Clayton and owned by C.T. Patterson & Co.
Cahn's Typhoon II was a known "mudder", and the rains poured on Derby day. But the horse, under "Boots" Garner, caused a six minute delay with nervous wheeling as the starter waited for the lineup to steady. Still, Typhoon II plunged to the lead immediately.
Ornament spent the entire race trying to catch Typhoon II. In the stretch they dueled like gladiators until Typhoon won the upset by a neck.
Four Start 1898 Kentucky Derby
The second smallest lineup ever started the 1898 Kentucky Derby -- four. The story seemed to revolve around two jockeys, however; Willie Simms and Tom Burns. Aware that the two riders had an intense no love lost relationship, Churchill Downs official M. Lewis Clark gave them a pre-race warning: no rough stuff, or face long suspensions.