| Episode Number | Description | Who was voted off (highlight to see)
| 1 (1 hour) (Season Premiere) | In the fifth-season premiere, 20 two-person teams consisting of same-season entrants from "The Real World" and "Road Rules" compete for bragging rights to the best season ever. Eric Nies ("The Real World I") and Mark Long ("Road Rules I") host from Cabo San Lucas. | Jon and Beth from Real World 2: Los Angeles; Yes and Veronica from Road Rules 8: Semester at Sea
| 2 | Due to an impending hurricane, the day's events are cancelled---and the hotel's power goes out. A bit stir crazy, the cast throws a toga party, where "the Miz" makes a memorable impression on Sharon. Meanwhile, Belou cares for her baby; and Chadwick and Holly find other things to do. | no one
| 3 | The "RW" team makes a pact to split the prize money between all members and then vote off the weaker players. The Roadies, on the other hand, are a team in the midst of dissension. Also: the competition picks up with the Musical Inner Tube Challenge.
| no one
| 4 | The "inner-tube tango" continues. Also: the Real World and Road Rules teams hold meetings to decide which contestants get jettisoned. | Mike J. and Sharon from Real World 4: London; Piggy and Chadwick from Road Rules 6: Australia
| 5 | The teams compete in "Vertical Limit," a rope-climbing competition. Also: the Roadies try to become more unified by developing a new scheme for distributing the big money; and the Real Worlders contemplate ousting Stephen. | no one
| 6 | Dissension envelops the Real World team when the Inner Council votes off Stephen and Lindsay even though they aren't faring poorly. Also: the teams take part in the "Slam Dunk" challenge, during which they attempt to dunk a basketball while bungee jumping. | Stephen and Lindsey from Real World 7: Seattle; Mike L. and Flora from Real World 5: Miami; Chris and Belou from Road Rules 3: Europe; Adam and Jisela from Road Rules 10: The Quest
| 7 | The first half of the "Battle of the Seasons" is recapped. | no one
| 8 | Tara and Mike attempt to hide their burgeoning relationship from the others to no avail. Also: the teams are hit by "Montezuma's revenge," which affects almost everyone; and Mark and Eric reveal the next challenge: the Ladder of Death. | no one
| 9 | The teams tackle the "Ladder of Death" challenge, which will determine the final three teams in each inner circle; Mike and Theo have a verbal spat. | Becky and Norm from Real World 1: New York; Holly S. and Josh from Road Rules 7: Latin America
| 10 | An angry e-mail from Chadwick upsets Holly and divides the "Road Rules" team. Also, the teams take part in a cow-penning competition. | no one
| 11 | The teams undertake a "Rush Hour" challenge, which consists of moving cars around a grid in order to get one out. | no one
| 12 | The teams compete for a car in a competition that sees which can keep their hands or feet on a block of ice longest. Also: the "Miz" makes an appearance. | no one
| 13 | The teams take part in a quiz challenge called the "Sidekick Showdown," in which they answer questions about their partners. | no one
| 14 | The teams face the "blockhead" challenge, which requires them to build a structure from blocks for one of the teammates to stand on. Also: Sean develops a plan for every contestant to leave with part of the "handsome reward," but not everyone goes for it. | no one
| 15 | The teams take part in "Siamese Wrestling," which requires the partners to be strapped together. Meanwhile, Holly calls Chadwick because she's upset about Mike's rough play. | no one
| 16 (season finale) | In the fifth-season finale, one team receives the "handsome reward" and one lucky contestant walks off with a cool $50,000. | the winning team: Real World | third place: Danny and Kelley from Real World 9: New Orleans second place: Mike and Coral from Real World 10: Back to New York the ultimate team: Sean and Elka from Real World 6: Boston Inside the Inner Circle (1 hour) | The contestants from the fifth season look back at the challenges they faced. | |
