|Season Run||January 17 – April 3, 2000|
|Winner(s)|| Road Rules|
Real World/Road Rules Challenge
Challenge 2000 is a six-on-six Challenge format. The teams traveled via tour bus starting in Las Vegas, Nevada then moving to the eastern U.S., ending in Miami, Florida after competing in different individual challenges. Each time a team won an individual challenge, they won $10,000. After each mission won, the winning team would invest those 10K in the product of their choice through E-Trade. At the end, the winning team also won any money won in the stock market. The last mission would be for the right to keep the money collected in the pot, an additional cash prize and a car.
|2||Demolition Derby||Real World||Road Rules|
|3||Wheel of Wrestling||Real World||Road Rules|
|4||Snake Wrangling||Road Rules||Real World|
|5||Redneck Games||Road Rules||Real World|
|6||Mud Football||Road Rules||Real World|
|7||Swamp Buggy Racing||Road Rules||Real World|
|9||Homemade Swimsuit Contest||Real World||Road Rules|
|10||Stir Crazy||Road Rules||Real World|
|11||Handsome Reward||Road Rules||Real World|
|4||Scavenger Hunt||Road Rules||Real World||$6000|
- Both teams lost the Tobacco Free Challenge.
- Road Rules won the final challenge, winning brand new 2000 Nissan Xterras. They earned $60,000, while also winning $6,000 in the "Scavenger Hunt" mini-challenge and an additional $1,524 through their E-trade online investment, for a total bank of $67,524 with each team member receiving $11,254.
- Real World earned $40,000, while also winning an additional $985 through their E-trade online investment, for a total bank of 40,985 with each team member receiving $6,830.