|Real World/Road Rules Challenge|
|Season Run||November 9 – December 14, 1999|
|Winner(s)|| Road Rules|
Road Rules: All Stars
|1||Roller Derby||Road Rules||Real World|
|2||Bed Race||Road Rules||Real World|
|3||Bungee Jump||Road Rules||Real World|
|4||Las Vegas Talent Show||Real World||Road Rules|
|5||Boot Camp||Road Rules||Real World|
|6||Handsome Reward||Road Rules||Real World|
|1||Golden Dollar||Real World||Road Rules||Limo ride|
|Teddy Bear Steal||Real World||Road Rules||$3,000|
- Road Rules won the final challenge, earning a total of $39,680, with each team member receiving $6,613.
- Real World lost the final challenge, earning $10,240, while also winning an additional $3,000 in the "Teddy Bear Steal" mini-challenge, for a total bank of $13,240, with each team member receiving $2,206.
|The Challenge Seasons|
Road Rules: All Stars · Real World/Road Rules Challenge · Challenge 2000 · Extreme Challenge · Battle of the Seasons (2002)