No such problem for me:

D:\>perl -MIO::Socket::SSL=debug4 -e  "$sock=IO::Socket::SSL->new('whe
+reabouts.eecs.umich.edu:443') or die IO::Socket::SSL::errstr"

D:\>perl -MNet::SSLeay -e "print $Net::SSLeay::VERSION"
1.25
D:\>perl -MIO::Socket::SSL -e "print $IO::Socket::SSL::VERSION"
0.92
D:\>
[download]

Are you sure that you're running Net::SSLeay-0.61 ? I couldn't locate that version. If it exists it must be fairly old as version 1.00 was released over 8 years ago. Maybe that's where your problem lies.

Cheers,
Rob