Yes if you tell Disney your 2 reservation numbers and they have rooms that meet your schedule. It is in Disney's best and yours to stay in the same room. You can call reservations or use the Chat feature in
MDE. Let them know your 2 reservations and they are a "Continuing" reservation.
Also check when you arrive at the WL Front desk and remind them that you have 2 reservations. They may ask you to stop by the Front desk on the night before check-out day or in the morning of your first reservation to confirm that you are all set.
Dave