As Raw heads to Connecticut’s Mohegan Sun gaming resort this Monday, “Raw Roulette” will make its return after a nearly five-year absence. And if past Roulettes are any indication, the first Raw of the New Year could be the most unpredictable of 2008.

Originally devised by then-Raw General Manager Eric Bischoff, Superstars will “gamble” their matches on a spin of a gigantic wheel, full of various matches and stipulations. The Superstars must compete in whatever match the wheel falls upon.

The wheel’s categories of matches are decided by the Chairman and General Manager beforehand. The two previous incarnations of Raw Roulette in October 2002 and November 2003 have created very unique – and entertaining – competition among the Superstars.

In 2002 in Las Vegas, the wheel brought forth matches such as:

• A Vegas Street Fight, which involved a pair of giant dice as a weapon.
• A Vegas Showgirls Match, which involved current Raw GM William Regal and Goldust dressed in showgirl attire and makeup.
• An It’s Legal In Nevada Match, in which Steven Richards and Jerry “The King” Lawler fought to win a “ride” on The Godfather’s Ho Train.
• A combo Bra & Panties / Paddle on a Pole Match, in which Trish Stratus spanked Stacy Keibler with the paddle.

The 2003 edition of Raw Roulette in Salt Lake City saw unique matches such as:

• A Divas Steel Cage Match between Lita and Victoria.
• A Capture the Midget Match between The Hurricane and Rosey, in which they competed to capture a fleeing midget named Fernando throughout the night.
• A Strange Bedfellows Match, which paired fierce rivals on the same tag team against another team of unlikely partners.

The unpredictability of the wheel creates chaos for the Superstars, since they can’t prepare for their matches in advance. And with Superstars chasing Royal Rumble Match spots, championship gold or trying to keep their legendary careers alive, that one spin of the wheel can make a world of difference.

Who knows what entertaining chaos Raw Roulette will provide Monday at Mohegan Sun Arena? Tune in 9/8 CT on USA Network and find out live on Raw.