A Group Request is used when you want to request a tee time for more than a foursome.
There are a couple of ways to create Group Requests. You can set up a single request if you have anywhere from 5 to 32 players. Problems arise in the winter months when tee times are tight and some of the players have lots of points. The point weight becomes a factor. With this method, all of the players' points become a factor in getting a reservation.
There is a second way to create a Group Request where you can create multiple requests of smaller groups and group the players so that the players in each request are matched so they have fewer points as a request group. The restriction on this type of group request is that you have to be a member of the first group and the remaining requests must be for the exact same day and times and the same course selections. Using this method, there is no guarantee that all of the groups will play, or play on the same courses but the groups that play will play at the same time.
This is what the tee time help message is concerning two groups. Yes, it is possible and according to this the times will be the same for both groups. Also, you put your name in only on the first request (otherwise you would have to be in two places at once). The requests are linked by the ID of the requestor, not the name. I have done it this way and the system accepted it.