Bracket or Tournament Help

I have a question about doing a bracket or a tournament page..
This is in a DRag Race Format

Here is the jef of what Im trying to do, need help on best way to do this..

Lets say I have 10 racers, each racer puts in 5 cars each, then they want to run the cars 2 times makeing it a total of 100 cars..

Im not sure how to build a bracket that will allow me to do this with these features in mind:

One racer has 5 cars in the race, he races the car twice, so now he has 10 cars in total to run in the race.
The bracket has to allow me to put him in 10 times, something like this:
John-Chevy
John-Chevy2
John-Vette
John-Vette2
John-Mopar
John-Mopar2
John-Nova
John-Nova2
John-Truck
John-Truck2

Ok he has 10 cars in the race, we now have 9 other racers going to do the same way, now I need to randomly put all these drivers in a bracket or tournament format to were they race each other but they dont race themselfs. Which ever driver wins moves to the next bracket to race someone else that has won till the last car is left, even if one driver still hase several cars left because he hasnt lost with that man cars left.

The opions Im looking for are as follows: Once I put all the names and cars in, Im able to click a button that will sort all the cars randomly to a bracket format, once the race is run, I can click on the car that won and have a option to click won or loss, this will sort him to the next bracket , if possable a place to put in his et's allowing him to get lane choice in the next race if his time is lower than the next car he races. The bracket will sort +- the et's and light up that car for that race who gets lane choice.
All the races will run until there is no cars left, and we have a winner, I may have 5 cars left, and beat all the other cars..

Looking for all the help I can find for this, any help would be apperciated, and If your interested in a project, please let me know.. Thanks Roger