The Challenge · Season 2
Real World/Road Rules Challenge
Champion: Anne Wharton & Kalle Dedolph & Kefla Hare & Mark Long & Noah Rickun & Roni Martin
Season overview
Location
San Francisco
Aired
November 9, 1999
through December 14, 1999
Episodes
6
Players
12
Host
David Edwards
Cast type
All new players
Cast
| Place | Player | Result |
|---|---|---|
| 1st |  Anne Wharton Road Rules: Northern Trail | Winner |
| 1st |  Kalle Dedolph Road Rules: Islands | Winner |
| 1st |  Kefla Hare Road Rules: Down Under | Winner |
| 1st |  Mark Long Road Rules: USA - The First Adventure | Winner |
| 1st |  Noah Rickun Road Rules: Northern Trail | Winner |
| 1st |  Roni Martin Road Rules: Northern Trail | Winner |
| 2nd |  Beth Stolarczyk The Real World: Los Angeles | Runner-up |
| 2nd |  Janet Choi The Real World: Seattle | Runner-up |
| 2nd |  Jason Cornwell The Real World: Boston | Runner-up |
| 2nd |  Montana McGlynn The Real World: Boston | Runner-up |
| 2nd |  Nathan Blackburn The Real World: Seattle | Runner-up |
| 2nd |  Neil Forrester The Real World: London | Runner-up |