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The exception is not raised when loop.set_debug(False) on my linux box.
So I guess this may be not reproductible on all platforms.
The new attached test_cancel_2.py raises an exception while asyncio debug is false, by forcing one more iteration of the loop after the pending tasks list is empty.
Also with asyncio debug false and with test_cancel_2.py and after removing the last task from the initial tasks list (i.e. asyncio.Task(asyncio.sleep(10))):
 * with more_iterations = 2: the exception is raised, not often
 * with more_iterations = 3: the exception is raised, seemingly always
 * with more_iterations = 0: another exception, often;
 Exception ignored when trying to write to the signal wakeup fd:
 OSError: [Errno 9] Bad file descriptor