I'm not a fan of street racing myself - I'd rather do it at in the controlled environment at the track where it is safer and more fair. However, my favorite race was on a backcountry road with a really good buddy of mine. This is a deserted road, but we had several people watch the end of the road for cars anyways just to make sure there weren't any problems.
My buddy has a 1994 Mustang Cobra 5-speed with 3.73:1 limited slip rear end, headers with custom X-pipe, K&N cold air intake kit, Centerforce Dual friction clutch, and aluminum driveshaft. He has it sprayed now, but this race was before he had that. His car is damn fast.
This was long before the bimmer, so I was racing him in my Camaro - 5.7 liter, 3 speed automatic with 2.73:1 non-limited slip rear. Some more displacement over his 302, but with a bad transmission disadvantage and a severe rear gear handicap. I had full length headers and dual 2.5" exhaust with H-pipe, 650cfm carb, Edelbrock performer intake, CompCams cam, K&N filter, and some other little odds and ends.
We lined up and were flagged off by a buddy. My car transmission is fairly heavily modified and has a manual/automatic valvebody that basically overrides the shift points manually when you enter the manual mode (kinda like the steptronic, but it won't shift automatically if you try to overrev it). I had the left foot on the brake, first gear selected, and had the engine revved to about 2000 rpm - the best launch RPM for my car since it's right at the peak of the fat torque curve. When the flag dropped, I let off the brake and feathered on the throttle to avoid making the rear tires go up in a cloud of smoke. My buddy had launched hard and was accelerating fast. Once I was assured I had decent traction, I put the hammer down. I stayed with him - the front of my car about at the back of his door - through first gear. I shifted to second at 5500 rpm, tires squeal and regain traction, and she hunkers down. By now, my buddy is in third gear, but second is my car's sweet spot - she pulls hard and fast all the way to 5500, where I shift into third. Now, I'm pulling my buddy by close to a fender. We continue on accelerating on up to about 100 before we shut 'em down. I ended up beating my buddy by about a half a car length.
I consider that to be quite an accomplishment and am still proud of how my baby performed. His car is damn fast, and he's a great driver. Shortly after this, he put a nitrous fogger system on the car, and he always bugged me to race him after that. I don't do nitrous - it's against my moral code.