diff --git a/spec/std/object_spec.cr b/spec/std/object_spec.cr
index 3df134513ae2..43d1c009a19e 100644
--- a/spec/std/object_spec.cr
+++ b/spec/std/object_spec.cr
@@ -11,6 +11,8 @@ private class StringWrapper
   end
 end
 
+private EQ_OPERATORS = %w(<= >= == != []= ===)
+
 private class TestObject
   getter getter1
   getter getter2 : Int32
@@ -113,6 +115,19 @@ private class TestObject
     {key, value}
   end
 
+  # NOTE: these methods are a syntax error in older versions
+  {% if compare_versions(Crystal::VERSION, "1.12.0-dev") >= 0 %}
+    {% for op in EQ_OPERATORS %}
+      def {{ op.id }}(*args, **opts)
+        [args, opts]
+      end
+
+      def {{ op.id }}(*args, **opts, &)
+        [args, opts, yield]
+      end
+    {% end %}
+  {% end %}
+
   annotation TestAnnotation
   end
 
@@ -130,7 +145,10 @@ end
 
 private class DelegatedTestObject
   delegate :property1=, to: @test_object
-  delegate :[]=, to: @test_object
+
+  {% for op in EQ_OPERATORS %}
+    delegate {{ op.id.symbolize }}, to: @test_object
+  {% end %}
 
   def initialize(@test_object : TestObject)
   end
@@ -206,6 +224,22 @@ describe Object do
       delegated = DelegatedTestObject.new(test_object)
       (delegated["foo"] = "bar").should eq({"foo", "bar"})
     end
+
+    {% if compare_versions(Crystal::VERSION, "1.12.0-dev") >= 0 %}
+      {% for op in EQ_OPERATORS %}
+        it "forwards \#{{ op.id }} with multiple parameters" do
+          test_object = TestObject.new
+          delegated = DelegatedTestObject.new(test_object)
+          delegated.{{ op.id }}(1, 2, a: 3, b: 4).should eq [{1, 2}, {a: 3, b: 4}]
+        end
+
+        it "forwards \#{{ op.id }} with multiple parameters and block parameter" do
+          test_object = TestObject.new
+          delegated = DelegatedTestObject.new(test_object)
+          delegated.{{ op.id }}(1, 2, a: 3, b: 4) { 5 }.should eq [{1, 2}, {a: 3, b: 4}, 5]
+        end
+      {% end %}
+    {% end %}
   end
 
   describe "getter" do
diff --git a/src/object.cr b/src/object.cr
index 6687e19f424a..ba818ac2979e 100644
--- a/src/object.cr
+++ b/src/object.cr
@@ -1293,17 +1293,18 @@ class Object
   # wrapper.capitalize     # => "Hello"
   # ```
   macro delegate(*methods, to object)
-    {% for method in methods %}
-      {% if method.id.ends_with?('=') && method.id != "[]=" %}
-        def {{method.id}}(arg)
-          {{object.id}}.{{method.id}} arg
-        end
-      {% else %}
-        def {{method.id}}(*args, **options)
-          {{object.id}}.{{method.id}}(*args, **options)
-        end
+    {% if compare_versions(Crystal::VERSION, "1.12.0-dev") >= 0 %}
+      {% eq_operators = %w(<= >= == != []= ===) %}
+      {% for method in methods %}
+        {% if method.id.ends_with?('=') && !eq_operators.includes?(method.id.stringify) %}
+          def {{method.id}}(arg)
+            {{object.id}}.{{method.id}} arg
+          end
+        {% else %}
+          def {{method.id}}(*args, **options)
+            {{object.id}}.{{method.id}}(*args, **options)
+          end
 
-        {% if method.id != "[]=" %}
           def {{method.id}}(*args, **options)
             {{object.id}}.{{method.id}}(*args, **options) do |*yield_args|
               yield *yield_args
@@ -1311,6 +1312,26 @@ class Object
           end
         {% end %}
       {% end %}
+    {% else %}
+      {% for method in methods %}
+        {% if method.id.ends_with?('=') && method.id != "[]=" %}
+          def {{method.id}}(arg)
+            {{object.id}}.{{method.id}} arg
+          end
+        {% else %}
+          def {{method.id}}(*args, **options)
+            {{object.id}}.{{method.id}}(*args, **options)
+          end
+
+          {% if method.id != "[]=" %}
+            def {{method.id}}(*args, **options)
+              {{object.id}}.{{method.id}}(*args, **options) do |*yield_args|
+                yield *yield_args
+              end
+            end
+          {% end %}
+        {% end %}
+      {% end %}
     {% end %}
   end