Triathlons are marked on the map by a checkered flag. The player cannot be in any vehicle when entering the event. The player will be immediately airlifted into the sky and given a Parachute, and subsequently fall to the ground. Boats will be waiting in the sea or river below, and the racers will attempt to land in them. The boats are raced to a beach on the island, where there are supercars loaded with tanks of nitrous oxide waiting. The cars are then raced to the finish line.
- Outstanding wanted levels will be erased at the start of the race.
- Each race has three opponents. They all jump out of your airlift before you.
- Players can use any of the vehicles prepared for them, but once one is selected, you cannot switch it for another prepared vehicle or traffic vehicle.
- Players have 10 seconds to return to their vehicle, should they leave it before the finish line or the vehicle switch point.
- Players may sabotage other vehicles (popping tires, denting in wheels, so on), but are impossible to explode.
- Players will be disqualified if they kill the other racers.
- In the beginning, freefall past the other contestants, then pull your parachute. This will give you an early lead.
- It best to build up a very big lead on both freefall and the boat race because the vehicles have a high chance of fishtailing, specially at the start due to them being parked on dirt and gravel, with Luis having to drive uphill and sometimes overland before hitting pavement. Vehicles also have a tendency to flip, especially if they hit obstacles with nitrous activated.
- Once a competitor lands in a boat, he cannot be removed from it, even if he lands in the same boat Luis is trying to board.
- First prize grants the player $1,000. The game will also be saved and the player will be shown their time to completion. Triathlons can be repeated endlessly.
- In addition, as with This Ain't Checkers, Luis gets to keep whatever supercar he chooses to drive, although the nitrous function is disabled after the race and the vehicle cannot be used to enter another triathlon.