| July 24, 2008, 9:00 PM EDT | Roster must be trimmed to 10 players |
| August 7, 2008, 9:00 PM EDT | 2008 FFL Draft |
| August 20, 2008, 11:59 PM EDT | Roster must be trimmed to 22 players; designation of "redshirt" player |
| September 4, 2008, 6:55 PM EDT | Roster must be trimmed to 20 players; FFL regular season begins |
| December 8, 2008 | FFL regular season ends |
| December 18-22, 2008 | Fantasy Bowl IX |
| January 31, 2009, 11:59 PM EDT | Roster must be trimmed to 15 players |
| March 21, 2009 | Deadline for submitting suggested changes or amendments to fantasy league rules |
| April 30, 2009 | Deadline for voting on suggested changes to fantasy league rules |
| May 1-31, 2009 | Runoff voting on suggested changes to fantasy league rules, if necessary |