This is a listing of the horses that finished in either first, second, or third place and the number of starters in the Maryland Sprint Handicap, an American graded stakes race run on dirt over six furlongs at Pimlico Race Course in Baltimore, Maryland.[1]
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| Year | Winner | Second | Third | Starters |
| 2022 | Jaxon Traveler | Three Over Deuces | War Tocsin | 6 |
| 2021 | Special Reserve | Strike Power | Frosted Grace | 11 |
| 2020 | Karan's Notion | Baptize the Boy | Lewisfield | 14 |
| 2019 | New York central | Proforma | Lewisfield | 7 |
| 2018 | Switzerland | Long Haul Bay | Lewisfield | 9 |
| 2017 | Whitmore | A. P. Indian | Awesome Banner | 9 |
| 2016 | Always Sunshine | All Star Red | Rockinn On Bye | 7 |
| 2015 | Sandbar | Service For Ten | Happy My Way | 8 |
| 2014 | Happy My Way | Lemon Drop Dream | Service for Ten | 6 |
| 2013 | Sage Valley | Hardened Wildcat | Laurie's Rocket | 10 |
| 2012 | Hamazing Destiny | Band Box | Action Andy | 10 |
| 2011 | Ventana | Immortal Eyes | China | 9 |
| 2010 | Taqarub | Roaring Lion | Ravalo | 10 |
| 2009 | Ravalo | Silver Edition | Celtic Innis | 7 |
| 2008 | Starforaday | Suave Jazz | Cognac Kisses | 8 |
| 2007 | Diabolical | Talent Search | Semaphore Man | 7 |
| 2006 | Friendly Island | Celtic Innis | Gaff | 7 |
| 2005 | Willy o'the Valley | With Distinction | Take Achance On Me | 8 |
| 2004 | Gators N Bears | Highway Prospector | Sassy Hound | 9 |
| 2003 | Pioneer Boy | Sassy Hound | Highway Prospector | 7 |
| 2002 | Snow Ridge | Smile My Lord | Clever Gem | 7 |
| 2001 | Disco Rico | Flame Thrower | Istintaj | 6 |
| 2000 | Dr. Max | Moon Over Prospect | Crucible | 7 |
| 1999 | Yes It's True | The Trader's Echo | Purple Passion | 8 |
| 1998 | Richter Scale | Trafalgar | Original Gray | 7 |
| 1997 | Cat Be Nimble | Political Whit | Excelerate | 7 |
| 1996 | Forest Wildcat | Kayrawan | Demaloot Demashoot | 9 |
| 1995 | Commanche Trail | Goldminer's Dream | Marry Me Do | 6 |
| 1994 | Secret Odds | Honor the Hero | Linear | 10 |
| 1993 | Senor Speedy | He Is Risen | Who Wouldn't | 7 |
| 1992 | Potentiality | Smart Alec | Boom Towner | 9 |
| 1991 | Jeweler's Choice | Shuttleman | Hadif | 5 |
| 1990 | Norquestor | Kechi | Americo's Bullet | 9 |
| 1989 | King's Nest | Silano | Regal Intention | 6 |
| 1988 | Fire Plug | Harriman | High Brite | 6 |
| 1987 | Purple Mountain | Little Bold John | Berngoo | 6 |