You are allowed 2 waitlist requests per UY. So yes, you can put those in. If one fills, then you’d want to cancel out the other since they are for different dates.
When they are for the same dates, and one fills, it cancels the other automatically.
Remember, all dates need to fill and the more days in one the harder it is. So, keep checking the website and get booked the days you know you want and adjust the websitel