To many variables to do it in the real world.
Most Semi's actually do not have the clearance for any car to safely pass under it. The Semi's in The Fast and the Furious, as well as Hardcastle and McCormick both were jacked up, under controlled situations. In the real world, the only trailer you might be able to get under is a log truck. That being said, there is a reason why those Semis were jacked and it was done in a controlled environment (with stuntmen). Roads are not perfect usually. Even if they are, there are still slight rises and dips, bumps, etc that will make cars and trucks do different things. If you were able to squeeze your X under a Semi while moving, you would have very little clearance to start with. Then if the Semi hits a slight bump, and is carrying a load, the front of the trailer might start to come down a little due to the trucks suspension, then as you hit the bump you start to go up just as the back of the trailer starts to go down. It would be a mess.
Now, would I do it in a controlled situation? Maybe. I would want no one else on the road, constant radio contact with the truck, a plan that if he bails he goes one way, I do the other, and I would want my X slammed as low to the ground and his truck jacked as high as safely possible. And then maybe at 10 miles per hour.