While I also recommend not to do this, I still like to try to answer your original question:
Java has a classloader hierarchy, so if you have both JARs in different levels of the hierarchy, the classloader defines its precendence. Most popular example is the web application classloader hierarchy (Tomcat for example), where application classes have a higher priority than the comtainer classes (if both are applicable).
If you have both JARs in the same classloader (same level), the filesystem determines the order, which is unreliable from the developer's point-of-view, so consider it to be random. Only one loads, but you don't know which, and will maybe not even get errors from dependency problems. If you get dependency problems, they may be java.lang.Errors, such as VerifyError, NoClassDefFoundError, NoSuchMethodError.