The Winterfest 2006 qualifying season began on October 28th, 2006, with a reset of the guild ladder. After five weeks, at December 11th, 2006, the top thirty-two ranked teams were to qualify for the season-ending playoffs (Winterfest 2006 Season Final Ladder Results). The swiss rounds took place on Saturday, December 15th, 2006 followed by the single elimination on Sunday, December 16th, 2006.

The Winterfest 2006 Season was the last tournament where the top ranked guilds at the end of the season's ladder were qualified for the playoffs.

Players were only allowed to use Core or Nightfall skills for their character builds during the playoffs. Any guild found using non-format skills in a match will cause that match to be forfeited. If this occurred a second time, that guild was disqualified from the playoffs and forfeit all prizes.

Players could create Assassins or Ritualists as their primary class but may only use skills on the allowed list. Weapons, armor, and runes were allowed from all 3 expansions.

• 1st place: Permanent Gold Cape trim for guild, Guild name and roster posted on Winterfest in-game trophy, Complete set (10) of wintergreen candy cane items.
• 2nd-16th place: Silver Cape trim for guild, Set of 9 to 5 wintergreen candy cane items (depends of the final standings position).
• 17th-32nd place: Bronze Cape trim for guild, Set of 5 to 1 wintergreen candy cane items (depends of the final standings position).

• Round 1: Isle of Solitude, 16:00 GMT.
• Round 2: Isle of Wurms, 17:00 GMT.
• Round 3: Corrupted Isle, 18:00 GMT.
• Round 4: Uncharted Isle, 19:00 GMT.
• Round 5: Frozen Isle, 20:00 GMT.

At the end of the swiss rounds, the top 8 guilds (based upon win loss results and strength of opponent tie-breakers) moved on to the single elimination quarter-finals (in a best 2 out of 3 battles) that took place on Sunday, December 17th 2006.