So stick your finger over a straw and dunk it in a drink. The air can't escape and will hold the water out. The plumbing under the pool is horizontal and will glug glug glug full again, but once the pipe angles upward, water won't be able to push air out of the way. Water can be in the horizontal pipe, well below the frost line, even for you in Canada. But the rest of the pipe is empty and can't freeze above the frost line. Places south of you don't even need to fully empty the pipe, just push the water down far enough that it cant freeze. For me that's about 3 feet worth of my 8 ft deep plumbing.