diff --git a/spec/sales_backend_spec.cr b/spec/sales_backend_spec.cr
index a5a6b20..8b5bc67 100644
--- a/spec/sales_backend_spec.cr
+++ b/spec/sales_backend_spec.cr
@@ -83,6 +83,12 @@ describe SalesBackend do
     address_state = Array(Address).from_json(Global.response.not_nil!.body)
     expected_address_state = Array(Address).from_json(new_address_str)
     (address_state.to_json == expected_address_state.to_json).should be_true
+    delete "/user/address", headers, new_address_str
+    Global.response.not_nil!.status_code.should eq(200)
+    get "/user/address", headers
+    Global.response.not_nil!.status_code.should eq(200)
+    address_state = Array(Address).from_json(Global.response.not_nil!.body)
+    address_state.size.should eq(0)
     get "/user/tokens", headers
     Global.response.not_nil!.status_code.should eq(200)
 
diff --git a/src/sales_backend/address.cr b/src/sales_backend/address.cr
index 7b9c3ba..4093577 100644
--- a/src/sales_backend/address.cr
+++ b/src/sales_backend/address.cr
@@ -48,4 +48,10 @@ class Address
         end
         return cmp
     end
+    def == (other : Address)
+        0==(self<=>other)
+    end
+    def != (other : Address)
+        0!=(self<=>other)
+    end
 end
\ No newline at end of file
diff --git a/src/sales_backend/http/user.cr b/src/sales_backend/http/user.cr
index e049f46..23ab840 100644
--- a/src/sales_backend/http/user.cr
+++ b/src/sales_backend/http/user.cr
@@ -153,7 +153,13 @@ delete "/user/address" do |context|
     if old_list.nil?
         addresses=Array(Address).new
     else
-        addresses=old_list-addresses
+        addresses=old_list.select do |v|
+            isin=false
+            addresses.each do |va|
+                    isin |= v==va
+            end
+            !isin
+        end
     end
     user_file.addresses=addresses
     File.write(Statics.data_path+"user/"+user.email,user_file.to_json)