May 1996: Jerry Bailey on Grindstone waves to the crowds as a handler leads the horse off the track after winning the Kentucky Derby at Churchill Downs in Louisville, Kentucky. Mandatory Credit: Simon Bruty /Allsport Date created:
Over the last 25-years, all but one winner of the Kentucky Derby has gone on to race at Pimlico in the Preakness. The only exception during that time frame was Grindstone, the 1996 Derby winner that was retired five days after the Derby due to bone chips in his knee. The other 24 horses that have gone on to race in the Preakness have had a good deal of success. Since 1986, nine Derby winners have won at Pimlico, six have finished 2nd, and three have finished 3rd, for an overall in-the-money success rate of 18-for-24 (75%).
Below is a list of Kentucky Derby winners and their Preakness finish since 1986.
| Year | Derby Winner | Preakness |
| 2010 | Super Saver | 8th |
| 2009 | Mine That Bird | 2nd |
| 2008 | Big Brown | 1st |
| 2007 | Street Sense | 2nd |
| 2006 | Barbaro | 9th |
| 2005 | Giacomo | 3rd |
| 2004 | Smarty Jones | 1st |
| 2003 | Funny Cide | 1st |
| 2002 | War Emblem | 1st |
| 2001 | Monarchos | 6th |
| 2000 | Fusaichi Pegasus | 2nd |
| 1999 | Charismatic | 1st |
| 1998 | Real Quiet | 1st |
| 1997 | Silver Charm | 1st |
| 1996 | Grindstone | DNS |
| 1995 | Thunder Gulch | 3rd |
| 1994 | Go for Gin | 2nd |
| 1993 | Sea Hero | 5th |
| 1992 | Lil E. Tee | 5th |
| 1991 | Strike the Gold | 6th |
| 1990 | Unbridled | 2nd |
| 1989 | Sunday Silence | 1st |
| 1988 | Winning Colors | 3rd |
| 1987 | Alysheba | 1st |
| 1986 | Ferdinand | 2nd |
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