High Stakes (North American and Australian title), also known as Road Challenge (European and Brazilian title), Conduite en état de liberté (French title) and Brennender Asphalt (German title), was released in the summer of 1999.

High Stakes introduced several new types of gameplay: High Stakes, Getaway, Time Trap, and Career. High Stakes is a racing mode (within Career) in which the reward was the losing player's car. Getaway requires the player to outrun numerous pursuing police vehicles for a given time period. Time Trap is where the racer has to finish a certain amount of laps within the time limit, with police cars trying to slow them down. Career mode incorporates a monetary reward system that allows a player to purchase vehicles and performance upgrades while earning cash by racing in a chronological set of tournaments. Another innovation is the introduction of damage models. Vehicles which have been involved in accidents featured visibly crushed car bodies and suffered from performance penalties. After a race in Career mode, the player is given the option to purchase repairs. The mode also allows players, for the first time, to upgrade cars, although the feature simply consists of switching between three upgrade levels for each car.

The PlayStation version of the game, released some months before the PC version, features improved gameplay. Only all-new tracks were implemented without the additional rehashes from NFS III in the PC version. Additionally, the AI in the game was more advanced; the five AIs known as Nemesis, Bullit, Frost, Ranger, and Chump featured different driving characteristics (i.e. Nemesis would hound the player until a slipup occurs, whilst Bullit exhibits a more aggressive style, occasionally ramming into the player's vehicle). Also, The Aston Martin DB7 was in the game at release, while the PC version required that players would need to download it online to put it in the game. In the PlayStation version, the McLaren F1 GTR was based on the 1997 Long Tail, while the PC version was based on the original 95/96 version.