The Distinguished Service Medal was an award presented by the Simming League in recognition of sustained outstanding service to the League. Nineteen individuals won DSMs during the lifetime of the award, 2006-11.
Laureates
| Laureate | Date | Citation |
| Charles Star of Independence Fleet | April 2011 | For service as chair of the 2011 SciWorld Convention and as Chief Editor of SimEnc. |
| Chas Hammer of Trek Online | March 2011 | For service as the Simming League Administrator. |
| Lyra Rose of Verak Nor | June 2008 | For service as the Chief Editor of SimEnc. |
| Janus of PBEM Players | June 2008 | For outstanding writing, including coverage of the SciWorld Online Convention. |
| Philip “Frug” Nicolcev of Thar Shaddin | June 2008 | For technical and administrative support to the Simming League. |
| Jonathan Daniels of Star Wars Unleashed | June 2008 | For managing chat rooms and social media for the Simming League. |
| Tom Leyton of Federation Sim Fleet | June 2008 | For assistance organizing the 2008 SciWorld Online Convention. |
| Sero of Capricorn Group | June 2008 | For outstanding contributions to the Simming League newsletter. |
| Kaarin Aalborg of Ajje Games | June 2008 | For assistance organizing the 2008 SciWorld Online Convention. |
| Eklan of Star Fleet On-Line | March 2007 | For service as a Simming League Magistrate. |
| Thomas Wallace of Taskforce 254 | March 2007 | For service as a Simming League Magistrate. |
| Tom Ryder-Morgan-Farr of Siren Fleet | March 2007 | For service as the President of the Simming League. |
| AOM Teal Fox of New Worlds Project | December 2006 | For service as the Simming League IT Guru. |
| Drew Ketchen of USS Thall | December 2006 | For outstanding contributions to the Simming League newsletter. |
| Jay Truce of Federation Sim Fleet | December 2006 | For service as the President of the Simming League. |
| Goran Agar of Federation Sim Fleet | December 2006 | For service as the President of the Simming League. |
| Xaero of Star Fleet On-Line | December 2006 | For service as the Simming League IT Guru. |
| Avron M’rees of USS Hawkeye | December 2006 | For service as the editor of the Simming League Digest. |
| Jack Carter of Alpha Fleet | November 2006 | For service as the Simming League graphics wizard. |