It will turn into 19.95 to keep the same psychology. Many stores already vary the last digit to mark the status of the item. Such as 97 for clearance items and so on.
It's so it doesn't cross the subconscious barrier of "under 20 dollars". $99.99 doesn't cross the subconscious barrier of $100 for example. It's probably been A/B tested to death, since it's so widespread among retailers.
In New Zealand our lowest denomination is 10c but retailers still use that pricing tactic. Electronic card transactions are very popular here and they are charged to the advertised price while cash transactions are simply rounded to the nearest 10th.