1999

Renault, Williams engine supplier for most of the 1990s, left Formula One at the end of the 1997 season. With no major engine suppliers available, Williams were forced to sign a contract to run customer engines for the 1998 and 1999 seasons. In 1998 the team failed to win a race for the first time in a decade. For the 1999 season, in the hope of attracting more investors to the underperforming team, Frank Williams agreed a driver swap with CART team owner Chip Ganassi, in which Ganassi's 1997 and 1998 CART champion driver, Alessandro Zanardi, would return to Formula One and Montoya would take his place in the competitive American series.

While Zanardi had a miserable year in Formula One, Montoya, with Honda power and a great Reynard chassis at his disposal, took the American motorsport scene by storm. He took the 1999 title in his rookie year, something accomplished six years earlier by former Formula One Champion Nigel Mansell.

The season that saw Montoya crowned as the youngest ever CART FedEx Championship Series Champion at the age of 24 was closely fought, especially with

Dario Franchitti who led the championship going into the final race in California. Both drivers finished the season with equal number of points but having won seven races to the Scotsman's three decided the title in the Colombian's favor. However, the CART rookie also attracted criticism - notably from Michael Andretti and his team - for his aggressive style of driving.  Montoya still had a contractual relationship with Williams and after his impressive rookie season the Grove-based team were keen for him to drive for them in Formula One. However, the young Colombian decided to race in the US for one more year. 

2000

In 2000 the Ganassi team switched to Toyota engines and Lola chassis. The package was strong for ovals and high speed tracks, but was less well suited to street and most road circuits. Toyota’s engines were not yet reliable and often failed the team. Despite this, Montoya led more laps than anyone else and took the maiden victory for a Toyota engine in the series. He was also the most popular driver, but in a season where he failed to finish in 40% of the races, he was out of contention for the championship.

That season the Ganassi team also competed in the prestigious Indianapolis 500 race, part of the rival Indy Racing League series. Media and drivers were critical of the way Juan Pablo approached the Brickyard, many IRL drivers labelled him as reckless and predicted an early retirement from the race. The media activity around the event was intense, with Montoya and his CART teammate Jimmy Vasser being the first CART drivers to "cross-over" to drive in the Indy 500. Despite public warnings from two-time Indy 500 winner Al Unser, Jr. claiming that if a driver doesn't respect the Indianapolis Motor Speedway, the place "will bite you - hard" Montoya shrugged off the advice claiming that all four corners were exactly the same and that the track required less attention than the road courses in the CART series and in European racing.

In the event, the Colombian star led 167 of 200 laps and claimed top honours at the end of the 500 mile race, taking an easy victory on his first attempt. He was the first to do so since Formula One World Champion Graham Hill in 1966 and was the first Colombian winner. His compatriot Roberto José Guerrero had previously finished twice as runner up.

Montoya also won CART's equivalent of the Indy 500, the U.S 500. Juan's victory marked his ninth and Toyota's first win in the CART (Champ Car World Series)series.

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