AmaTIGRESS had the right idea but I had the hardest time finding that "sweet spot."
So, here's how I got to the exact spot:
With the 2nd controller, move to the left until your pawn is just touching the left edge of the arrow markers (not all the way to the side line.) Then point your arrow to the small white space between the R and the Y in SORRY!
After you release the pawn, it should follow the curve so the pawn ends up in the Sorry zone. I also found in this spot, you only had to use a medium force - just a flick with the joystick that was more of my natural motion.
Also, be careful to keep your winning pawns out of the way - just position them right up the middle.