There's a few layers which you can simulate this at. The easiest would be if your two servers listen on two distinct TCP ports. In that case, you could run two tcp proxies, and stop/pause one when you want to simulate a failure. For Windows I would suggest using tcpTrace to do this.
Another option would be to have the two servers bound to two virtual NICs, which are bridged to the physical NIC. Of course if you have two physical NICs, you could bind each server process to a different physical NIC.
At a lower level, you can ran a WAN simulator. Most simulators allow you to impair specific types of traffic or specific ports. One such simulator is Packetstorm.
One other method which I would suggest is attaching a debugger to one process, and halting all threads on the process with the debugger. Often, a process doesn't die, but gets stuck in garbage collection, or in a loop. As the sockets don't close, many 'high availability' solutions won't automatically failover.