The Kalendra Award
Awarded to a simmer who has performed (on more than one occasion) devious, unexpected plot twists. The simmer must have shown an ability to surprise their colleagues with clever plot twists that were relevant and plausible, given a particular plot.
Introduced for the '99 ceremony.
| Simmer | Ship/Awarded By | Ceremony |
| Lt. Cmdr. Toni Turner | USS Challenger | 2006 |
| Cmdr. Daydan Taboo | USS Constitution | 2006 |
| Lt. Cmdr. Eden Redstone | USS Discovery | 2006 |
| Cmdr. Samuel Nigel Perkins | USS Triumphant | 2006 |
| Lt. Cmdr. Paul Diamond | USS Victory | 2006 |
| Lt. Cmdr. Sam Nigel Perkins | USS Kodiak | 2005 |
| Capt. Jessa K. Anassasi | Capt. Xan Hebron | 2002 |
| Civ. Hamlet of Dane | UFOP Staff | 2000 |
| Capt. Maela Jolon | Fleet Capt. Elinor | 1999 |
