The award presentations are normally made in May of the year after the award designation; for example, the 2004 awards were presented in May 2005. Past recipients of the E.H. Harriman Award were:
| Year | Group | Gold medal | Silver medal | Bronze medal |
|---|---|---|---|---|
| 1938 | Norfolk and Western Railway | |||
| 1989 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | ||||
| 1990 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | ||||
| 1991 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | Belt Railway of Chicago | |||
| 1992 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | ||||
| 1993 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | ||||
| 1994 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | ||||
| 1995 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | Belt Railway of Chicago | |||
| 1996 | A | Norfolk Southern | Burlington Northern and Santa Fe | CSX Transportation |
| B | New Jersey Transit Rail Operations | Illinois Central | Kansas City Southern | |
| C | Texas Mexican | Providence & Worcester | New York, Susquehanna & Western | |
| S&T | Port Terminal Railroad Association | Belt Railway of Chicago | Houston Belt & Terminal Railway | |
| 1997 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | ||||
| 1998 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | ||||
| 1999 | A | Norfolk Southern | Burlington Northern Santa Fe Railroad | CSX Transportation |
| B | Illinois Central Railroad | Kansas City Southern Railway | NJ Transit | |
| C | Bessemer and Lake Erie Railroad | Duluth, Winnipeg and Pacific Railroad | Guilford Rail System | |
| S&T | Belt Railway of Chicago | Port Terminal Railroad Association | Patapsco and Back Rivers Railroad | |
| 2000 | A | Norfolk Southern | ||
| B | Kansas City Southern Railway | |||
| C | Gateway Western Railway | |||
| S&T | Belt Railway of Chicago | |||
| 2001 | A | Norfolk Southern | ||
| B | ||||
| C | ||||
| S&T | Belt Railway of Chicago | |||
| 2002 | A | Norfolk Southern | ||
| B | Metra | |||
| C | ||||
| S&T | Terminal Railroad Association of St. Louis | Conrail | ||
| 2003 | A | Norfolk Southern | ||
| B | Metra | Soo Line Railroad | ||
| C | Iowa Interstate Railroad | |||
| S&T | Terminal Railroad Association of St. Louis | Conrail | ||
| 2004 | A | Norfolk Southern | BNSF Railway | Union Pacific Railroad |
| B | Metra | Soo Line Railroad | Illinois Central Railroad | |
| C | Guilford Rail System | Wheeling and Lake Erie Railroad | Providence and Worcester Railroad | |
| S&T | Terminal Railroad Association of St. Louis | Conrail | Alton and Southern Railway | |
| 2005 | A | Norfolk Southern | BNSF Railway | CSX |
| B | Canadian Pacific's U.S. subsidiary (formerly Soo Line Railroad) | Kansas City Southern | Metra | |
| C | Florida East Coast Railway | Pan Am Railways | Elgin, Joliet and Eastern Railroad | |
| S&T | Terminal Railroad Association of St. Louis | Conrail | Belt Railway of Chicago | |
| 2006 | A | Norfolk Southern Railway | CSX Transportation | BNSF Railway |
| B | Kansas City Southern Railway | Canadian Pacific Railway's United States subsidiary | Long Island Rail Road | |
| C | Florida East Coast Railway | Central Oregon and Pacific Railroad | BNSF Suburban Operations in Chicago | |
| S&T | Birmingham Southern Railroad | Conrail | Terminal Railroad Association of St. Louis | |