My co-worker has a Surface Pro, so I borrowed that. It is about 1.5" too long to fit in that padded pocket, but it will still fit in the compartment easily. (That compartment is exactly the size of an iPad.)

I'm not sure about the headphones and everything, as my noise cancelling are earbuds. If you only have a Surface on the laptop side, I think it will be close, but I think it will work. Even though the Small Byte is divided it up more, it does seem to be roomier than the Speedy Mini. I think the two zippers help in that aspect.