I thought $ works on Windows with carriage returns but it seems it doesn't...

It does. The OS-specific line terminator character(s) is/are translated somewhere in Perl's I/O layers to a common  \n newline character (which, IIRC, is 0x0a linefeed) — unless you're using binmode or some other form of raw read/write. The following code should execute identically (I believe) under any OS (I'm running this under Windoze 7):

c:\@Work\Perl\monks\marek1703>perl -wMstrict -le
"use Data::Dump qw(pp);
 ;;
 for my $s (qq{foo\r\n}, qq{foo\r}, qq{foo\n}, qq{foo}) {
   if ($s =~ /foo$/) {
     print 'matched: ', pp $s;
     }
   else {
     print 'no match: ', pp $s;
     }
   }
"
no match: "foo\r\n"
no match: "foo\r"
matched: "foo\n"
matched: "foo"
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See definition of  $ in Regular Expressions - Metacharacters and its general discussion in perlre and perlretut. The match failures are due to the  \r stuck in the middle of things.

Also consider the following, which I also expect would work the same on any OS (it certainly works under Windows):

use warnings;
use strict;


while( <DATA> ) {
    if (/^"([^"]{2,})","(\d)","(.+)"$/) {
        chomp;
        my ($one, $two, $three) = ($1, $2, $3);
        print "matched: ``$_'' ('$one', '$two', '$three') \n";
        }
    else {
        print "no match: ``$_'' \n";
        }
    }


__DATA__

"Sonntag, 26.05.2013 - 13:13:27","0","Lieber Herr % , & text text with
+ some %special characters"
xyzzy
"Mittwoch, 05.06.2013 - 18:12:09","0","Besten Dank, & hat prima geklap
+pt. {Greetings!}"
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