This is a way you could do it using Template Toolkit. Using a template system allows you to keep the HTML out of your code and will also handle writing the new files for you:

use Template;
my $template = Template->new;
my $tmpl = 'table.tmpl';

my %names;
while ( my $line = <DATA> ) {
    chomp $line;
    my ($name,$item,$answer) = ($line =~ m/^(\w+)\s+(\w+)\s*-\s*(.*)/)
+;
    push( @{ $names{$name} }, { item=>$item, answer=>$answer } );
}
for my $name ( keys %names ) {
    my $table = { title=>$name, rows=>$names{$name} };
    $template->process( $tmpl, $table, "$name.html" )
        || die $template->error();
}

__DATA__
Filename1 Item1 - Answer
Filename1 Item2 - Answer
Filename2 Item1 - Answer
Filename2 Item2 - Answer
[download]

This will create two new files "Filename1.html" and "Filename2.html".

The content part of the template file "table.tmpl" would look like this:

<h1>[% title %]</h1>

<table>
[% FOREACH row IN rows %]
    <tr>
        <td>[% row.item %]</td>
        <td>[% row.answer %]</td>
    </tr>
[% END %]
</table>
[download]

Obviously, you need to add the html and body tags around this, and you can also add CSS and other static elements.