I believe your problem is that you are not attempting to match the line from the file, but rather the filename itself.

Try something like this instead, to read and parse lines from a file:

use FileHandle;
my $fh = new FileHandle;
open($fh, "<", $file) or die "Unable to open file '$file' ($!)\n";
while (my $line = <$fh>) {
    chomp $line;
    if ($line =~ /(<IMG.*?BR>)...(Figure\d*)/i) {
        # You got a match
    }
}
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