Has your friend tried the netstat command, probably as netstat -a to check listening ports, to confirm that the game server is listening at all? (Run that on the same machine as the server.) It has been a long time since I have used Windows, so you may want to check the output of netstat /? or netstat -? for other hints on using that command.
Your descriptions sound suspiciously like a series of keystrokes entered at some prompt. What are you typing those keystrokes into? The best solution here may involve Expect rather than Perl if you are trying to automate interacting with a simple shell program. Perl will work much better if you are wanting to actually send network packets directly.