Miami - The Road Rules cast posed as house cleaners and stole the Miami's cast eight-ball. They did so successfully. Timmy fooled Miami's Dan and Cynthia who were obviously suspicious of the unannounced cleaning crew. Europe - No face-off. Islands vs. Real World: Boston - The casts competed in a series of competitions in San Juan, Puerto Rico. Prior to each event, two random people from the Boston cast were required to sit out in order for the number of people on each team to be even. The first event was to get each teammate through a web of wires. Each teammate had to pass through a different hole and could not touch the sides. The second event was to get each teammate from one platform to another using only a piece of wood that was not long enough to bridge the gap. The third event was to have all 5 teammates balance on a wooden cube at the same time. The fourth event was to have each teammate climb a wooden wall, and the final event was a tug of war. The Real World Boston won the first three events, and the Road Rules Islands cast won the final two. Syrus, while competing in the second mission, injured his shin attempting to jump from one platform to the other without using the board. The Islands crew, who desperately needed money at that time asked the Boston cast to split their winnings. The Boston cast declined to do so. They also played paintball with a team of former Road Rulers from different seasons at the beginning of their season. (Los/Christian/Devin/Effie/Michelle with special guest Timmy as a referee) The previous Road Rulers won two of the three contests, leaving the Road Rules Islands cast with only $400. Northern Trail vs. Road Rules: All Stars - The casts competed in a series of Olympic-themed games including luge, ski jumping, and figure skating. The Olympic-theme was due in part to the fact that the casts were competing in the Olympic facilities at Lake Placid, New York. The competition consisted of 5 events: a two-man kayak, a one-man kayak, two individual luges, ski jumping, and figure skating. Each person had to compete in at least one event but could not compete in more than two. Road Rules won the two man kayak and the luge while the Real World All-Stars won the individual kayak