Yes, crossover/straight through does matter most of the time.
The way that I was taught it is that if you're switch has an uplink port, and you're connecting that port to a regular port on another switch, you would use a straight through.
If your switch doesn't have an uplink port, then you would need a crossover cable.
Now, I said that it matters most of the time which type of cable you use. I have heard of, but not used, switches that autosense the type of cable that you have, and can correct for if you use the wrong type. I don't know if that would be only on an uplink port, or if that would be on every port of a switch.
Edit: Reading my reply, I think it would be clearer with an example of what I'm trying to say.
Say you have 2-12 port switches. These switches each have uplink ports. You want to connect the two to each other. Using a straight-through cable, you can choose a port (1 through 12) on one to connect to the uplink port on the other. Using a crossover cable, you can choose a port (1 though 12) to connect to another port (1 through 12) on the other.
I hope that clarifies a little more.
