I would look at the parameters on which you DO want to delete, and work it something like this. (Based on the following)

use strict;
use Win32::OLE qw(in with);
use Win32::OLE::Const 'Microsoft Outlook';
$|++;
$Win32::OLE::Warn = 3; # Throw Errors, I'll catch them

my $OL = Win32::OLE->GetActiveObject('Outlook.Application')
        || Win32::OLE->new('Outlook.Application', 'Quit');

    my $NameSpace = $OL->GetNameSpace("MAPI");
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I used this to fill in some values:

my $Contacts =  $NameSpace->Folders("Personal Folders")->Folders("Cont
+acts");
 
    my @names = qw(Chuck Charles Charlie Chuckles);
    foreach my $name (@names){
        my $NewContact = $Contacts->Items->Add();
           $NewContact->{FirstName}=$name;
           $NewContact->{LastName}="Charbeneau";
           $NewContact->Save();
           print "Added $name\n";
    }
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And this to delete the names I don't like:

$Contacts =  $NameSpace->Folders("Personal Folders")->Folders("Contact
+s")->{Items};
    my $Cacharbes = $Contacts->Find("[LastName]=Charbeneau");
    my $cnt = 0;
    while (1) {
      if ($Cacharbes->{FirstName} eq "Chuckles"){
          $Cacharbes->Delete();
      }
      $Cacharbes = $Contacts->FindNext() || last;     
   }
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The thing is, the find and find next function only return a single item from the main collection.

Each item in a Contacts folder collection has a unique ->{EntryID} property, but it's not something you can remmber off the top of your head.

C-.