For many file types, there is a shell extension installed so that you can print using the (right-click) context menu from Windows Explorer. You can use these shell extensensions from Perl. (This uses Win32::API, which I think comes with Active Perl 5.8 and above.)

#!perl -w
use Win32 qw(SW_SHOWNORMAL);
use Win32::API;
use strict;
my $shellexec = Win32::API->new('shell32', 'ShellExecute', 'NPPPPI', '
+N')
  or die "cannot import ShellExecute: $!\n";

for my $filename (  "small.pdf", 
    "realfilebutunknownextension.qqt",
    "notanexistingfile.doc",
    "knownextbutnoprint.wpl") {
  my $result = 
    $shellexec->Call(0, "print", $filename, "", ".", SW_SHOWNORMAL);

  my $msg = ($result>32)?"Success": Win32::FormatMessage($result);

  printf "ShellExecute(, \"print\", \"%s\", ...) => %s\n", $filename, 
+$msg;
}
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This code checks to see whether the "print" action was started, but there's no way to tell whether it successfully finished.

You can see whether a file has an associated "print" action in Windows Explorer. Click on "Tools|Folder Options", then the "File Types" tab, and, for any extension, click "Advanced." Note that these usually just use command-line options to the associated windows application. For example, my PDF print command is:

"C:\Program Files\Adobe\Acrobat 4.0\Acrobat\Acrobat.exe" /p /h "%1"
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There are also inexpensive file viewers that you can get download, either as standalone applications or as ActiveX controls that you can control using Win32::OLE.

See this Google search, e.g.