Anything that's painless doesn't hurt at all. A painless medical procedure (like having blood drawn) might be a little scary, but it's actually very easy.
Getting your teeth cleaned at the dentist should be a painless process, although getting a filling sometimes hurts a little bit. A painless math test is simple and requires very little work or thought on your part — this is a figurative way to use painless, obviously, since no one would expect a math test to cause you physical pain, even if it's not your strongest subject.