diff --git a/app/models/alchemy/page/page_naming.rb b/app/models/alchemy/page/page_naming.rb
index 940b12ea86..8f21a0672b 100644
--- a/app/models/alchemy/page/page_naming.rb
+++ b/app/models/alchemy/page/page_naming.rb
@@ -25,6 +25,8 @@ module PageNaming
         after_update :update_descendants_urlnames,
           if: :saved_change_to_urlname?
 
+        before_save :destroy_obsolete_legacy_urls, if: :renamed?
+
         after_move :update_urlname!
       end
 
@@ -55,6 +57,11 @@ def update_descendants_urlnames
         descendants.each(&:update_urlname!)
       end
 
+      def destroy_obsolete_legacy_urls
+        obsolete_legacy_urls = legacy_urls.select { |legacy_url| legacy_url.urlname == urlname }
+        legacy_urls.destroy(obsolete_legacy_urls)
+      end
+
       # Sets the urlname to a url friendly slug.
       # Either from name, or if present, from urlname.
       # The urlname contains the whole path including parent urlnames.
diff --git a/spec/models/alchemy/page_spec.rb b/spec/models/alchemy/page_spec.rb
index 25c6f04954..17e6de4cd7 100644
--- a/spec/models/alchemy/page_spec.rb
+++ b/spec/models/alchemy/page_spec.rb
@@ -1689,6 +1689,18 @@ def copy_children_to(new_parent)
           expect(page.legacy_urls.pluck(:urlname)).to include("parentparent/parent/page")
         end
       end
+
+      context "if new urlname exists as a legacy url" do
+        it "will delete obsolete legacy_urls" do
+          expect(page.urlname).to eq("parentparent/parent/page")
+          page.update!(urlname: "other-name")
+          expect(page.legacy_urls.pluck(:urlname)).to include("parentparent/parent/page")
+          page.update!(urlname: "page")
+          expect(page.legacy_urls.pluck(:urlname)).to include("parentparent/parent/other-name")
+          expect(page.urlname).to eq("parentparent/parent/page")
+          expect(page.legacy_urls.pluck(:urlname)).not_to include("parentparent/parent/page")
+        end
+      end
     end
 
     describe "#update_node!" do