Snake Bit Achievement
Beat a Ferrari in a 1965 Shelby Cobra Daytona Coupe
This achievement is best earned in Free Play using a 1965 Shelby Cobra Daytona Coupe. From the main menu choose Free Play and in the menu choose "Select Track". Select any track you wish, generally the shorter the better. Then go to "Select Car" and choose the 1965 Shelby Cobra Daytona Coupe. Select "Game Options" and set Game Type to Circuit Race, Drivatars to 15, Drivatar Difficulty to New Racer, and Laps to 1.
Choose start race and when the track loads, select Starting Grid. Check to ensure there is at least one Ferrari on the list. If there is not, back out and start over, repeating until a Ferrari shows up. Start the race and you should easily come in first, unlocking this achievement. As long as at least one Ferrari finishes after you, a win is not actually required for this achievement.
The achievement will unlock naturally through normal game play if you select the 1965 Shelby Cobra Daytona Coupe as your car of choice in the Vintage Racing Icons Championship Series, which is the third series in the Vintage League.
Note that the 1965 Shelby Cobra Daytona Coupe is one of the most expensive vehicles in the game and is the only car this achievement can be earned with. If you don't have the money to purchase it, or don't wish to spend the money, there is currently a way to rent it even though typically it is not available for rent. To do this, follow the instructions above and when you get to selecting your vehicle, choose Rent Car and press on the first choice. This will drop you back to the Freeplay setup screen. Choose Select Car again, and this time go to Buy Car. Scroll to the 1965 Shelby Cobra Daytona Coupe, press to buy the car but at the Recommended Designs screen, press three times. This will drop you back to the Freeplay setup screen again, but you will have the 1965 Shelby Cobra Daytona Coupe as your rental. This is a bug in the game and may be patched at some point. If it is patched, you will need to purchase the Shelby to obtain this achievement.