Outlaw Racers

Description
Outlaw Racers is a racing game that came with three novel features at the time of release: a randomly generated city for each race, law enforcement that includes traffic cameras in addition to the police cars, and finally, a "persistent" universe where other cars are raced for money and bragging rights. However, the game can be boiled down to a simple "checkpoint" racing system, albeit in a city environment.
The game has a 3D accelerated option, and can actually use DirectX 5 if enabled.
A typical race has multiple checkpoints (flags) that must be passed through for money and to win the race. When all the flags are claimed, the race is over. However, there is no specific order in which those flags can be taken, allowing different strategies to make the most of a race. The player can for instance go for the closest flag, likely facing heavy competition going for the same goal, or they can aim for the farthest ones and try to clean them up while their competitors fight over the nearest flags.
The race is further complicated by the police chasing after the racers. The city also has traffic cameras that record offenses such as red light violations, driving on the wrong side of the road, and so on. If the cops manage to stop the player, they will fine them for all the recorded offenses and these will be automatically taken out of their "budget". If the player no longer has money, they are sent to jail and the race is over. Reaching flags first or bumping into cash trucks gives the highest amount of money.
Other vehicles wander the road in addition to police cars and cash trucks. There are also civilian vehicles, and five gray "armored cars" that will bump the player off the road if they run into them.
Finally, there's a "hyper transporter" system that will take the player's car from one city to another for a nominal fee, but it requires reaching the boarding point and waiting for it. It may not appear in every city.
As the city is randomly generated, the flags are never in the same place, and the three other opponents are thus rather unpredictable, making each race more or less unique.
The cars can also be upgraded with better tires, better engine, or just replaced with better cars, although the upgrade system stays quite simple. Cars can also be repainted and/or decorated with special decals (user bitmap is allowed).