TIMES – KENTUCKY DERBY ¼ MILE – SLOWEST No. Year Horse Finish Split ¼ MILE – FASTEST 1. 1899 His Lordship 4th :25.75 2. 1898 Lieber Karl 2nd :25.50 No. Year Horse Finish Split st th 2. 1901 His Eminence 1 :25.50 1. 1981 Top Avenger 19 :21.80 th th 2. 1903 Woodlake b 5 :25.50 2. 1975 Bombay Duck 15 :22.00 st th 2. 1905 Agile 1 :25.50 3. 1986 Groovy 16 :22.20 th th 6. 1896 First Mate 4 :25.00 3. 1968 Kentucky Sherry 5 :22.20 th 3. 1967 Flag Raiser 8th :22.20 6. 1904 Spanish Chestnut 16 :22.28 6. 1908 Bodemeister 2nd :22.32 6. 2001 Songandaprayer 13 th :22.25 6. 1909 Honour and Glory 18 th 7. 2005 Spanish Chestnut 16 th :22.28 :22.34 8. 2012 Bodemeister 2nd :22.32 9. 1996 Honour and Glory 18 th :22.34 ¼ MILE – SLOWEST LAST 30 YEARS (1987) rd 1. 1997 Free House 3 :23.57 ¼ MILE – FASTEST LAST 30 YEARS (1987) 1. 2001 Songandaprayer 13 th :22.25 ½ MILE – SLOWEST No. Year Horse Finish Split ½ MILE – FASTEST 1. 1899 Manuel 1st :51.25 2. 1901 His Eminence 1st :51.00 No. Year Horse Finish Split rd th 2. 1903 Woodlake b 3 :51.00 1. 2001 Songandaprayer 13 :44.86 nd th 4. 1898 Lieber Karl 2 :50.25 2. 1981 Top Avenger 19 :45.20 th th 5. 1908 Banridge 5 :50.20 2. 1986 Groovy 16 :45.20 st th 6. 1905 Agile 1 :50.00 4. 2013 Palace Malice 12 :45.33 nd th 6. 1907 Zal 2 :50.00 5. 2005 Spanish Chestnut 16 :45.38 th 6. 2012 Bodemeister 2nd :45.39 8. 1906 Hyperion II 4 :49.80 9. 1909 Wintergreen 1st :49.60 7. 1975 Bombay Duck 15 th :45.40 9. 1928 Misstep 2nd 8. 1978 Sensitive Prince 6th :45.60 :49.60 9. 2016 Danzing Candy 15 th :45.72 10. 1998 Old Trieste 10 th :45.75 ½ MILE – SLOWEST LAST 30 YEARS (1987) th 1. 2011 Shackleford 4 :48.63 ½ MILE – FASTEST LAST 30 YEARS (1987) th ¾ MILE – SLOWEST 1. 2001 Songandaprayer 13 :44.86 st 1. 1899 Manuel 1 1:17.75 2. 1908 Stone Street 1st 1:17.40 ¾ MILE – FASTEST nd th 3. 1907 Zal 2 1:17.00 1. 2001 Songandaprayer 13 1:09.25 nd th 4. 1898 Lieber Karl 2 1:16.50 2. 2005 Spanish Chestnut 16 1:09.59 th st 4. 1903 Woodlake b 5 1:16.50 3. 1985 Spend a Buck 1 1:09.60 st th 6. 1901 His Eminence 1 1:16.25 4. 2013 Palace Malice 12 1:09.80 st nd 7. 1912 Worth 1 1:16.20 4. 2012 Bodemeister 2 1:09.80 st th 7. 1918 Exterminator 1 1:16.20 4. 1968 Kentucky Sherry 5 1:09.80 st th 9. 1905 Agile 1 1:16.00 7. 2000 Hal’s Hope 16 1:09.99 st 8. 1963 Never Bend 2nd 1:10.00 10. 1909 Wintergreen 1 1:15.80 10 1928 Misstep 2nd 1:15.80 9. 1996 Honour and Glory 18 th 1:10.15 10. 1962 Sunrise Country 5th 1:10.20 th ¾ MILE – SLOWEST LAST 30 YEARS (1987) 10. 1981 Top Avenger 19 1:10.20 th 10. 1986 Groovy 16 th 1:10.20 1. 2011 Shackleford 4 1:13.40 1 MILE – SLOWEST ¾ MILE – FASTEST LAST 30 YEARS (1987) st 1. 2001 Songandaprayer 13 th 1:09.25 1. 1908 Stone Street 1 1:46.00 2. 1899 Manuel 1st 1:45.50 3. 1907 Zal 2nd 1:45.00 1 MILE – FASTEST nd st 4. 1918 Escoba 2 1:43.60 1. 1985 Spend a Buck 1 1:34.80 nd rd 5. 1928 Misstep 2 1:43.40 2. 2001 Congaree 3 1:35.00 nd th 6. 1898 Lieber Karl 2 1:43.25 3. 1996 Unbridled’s Song 5 1:35.16 st nd 7. 1901 His Eminence 1 1:43.00 4. 2012 Bodemeister 2 1:35.19 st th 8. 1929 Clyde Van Dusen 1 1:42.80 5. 1962 Admiral’s Voyage 9 1:35.20 st nd 9. 1905 Agile 1 1:42.75 6. 1963 Never Bend 2 1:35.40 st 6. 1952 Hill Gail 1st 1:35.40 10. 1912 Worth 1 1:42.60 8. 1976 Bold Forbes 1st 1:35.60 8. 1966 Kauai King 1st 1:35.60 1 MILE – SLOWEST LAST 30 YEARS (1987) th 10. 2016 Gun Runner 3rd 1:35.61 1. 1989 Houston 8 1:37.40 10. 1998 Real Quiet 1st 1.35.61 1 ¼ MILES – SLOWEST 1. 1908 Stone Street 1st 2:15.20 1 MILE – FASTEST LAST 30 YEARS (1987) st rd 2. 1907 Pink Star 1 2:12.60 1. 2001 Congaree 3 1:35.00 st 3. 1897 Typhoon II 1 2:12.50 4. 1899 Manuel 1st 2:12.00 1 ¼ MILES – FASTEST st st 5. 1918 Exterminator 1 2:10.80 1. 1973 Secretariat 1 1:59.40 st st 5. 1929 Clyde Van Dusen 1 2:10.80 2. 2001 Monarchos 1 1:59.97 st st 7. 1905 Agile 1 2:10.75 3. 1964 Northern Dancer 1 2:00.00 st st 8. 1928 Reigh Count 1 2:10.40 4. 1985 Spend a Buck 1 2:00.20 st st 9. 1919 Sir Barton 1 2:09.80 5. 1962 Decidedly 1 2:00.40 st 6. 1967 Proud Clarion 1st 2:00.60 10. 1912 Worth 1 2:09.40 7. 1996 Grindstone 1st 2:01.06 8. 2000 Fusaichi Pegasus 1st 2:01.12 1 ¼ MILE – SLOWEST LAST 30 YEARS (1987) 1. 1989 Sunday Silence 1st 2:05.00 9. 2002 War Emblem 1st 2:01.13 10. 2003 Funny Cide 1st 2:01.19 1 ¼ MILE – FASTEST LAST 30 YEARS (1987) 1. 2001 Monarchos 1st 1:59.97 .