diff --git a/spec/matchers/end_with_matcher_spec.cr b/spec/matchers/end_with_matcher_spec.cr
new file mode 100644
index 0000000..ea9a828
--- /dev/null
+++ b/spec/matchers/end_with_matcher_spec.cr
@@ -0,0 +1,284 @@
+require "../spec_helper"
+
+describe Spectator::Matchers::EndWithMatcher do
+  describe "#match?" do
+    context "with a String" do
+      context "against a matching string" do
+        it "is true" do
+          value = "foobar"
+          last = "bar"
+          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_true
+        end
+
+        context "not at end" do
+          it "is false" do
+            value = "foobar"
+            last = "foo"
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::EndWithMatcher.new(last)
+            matcher.match?(partial).should be_false
+          end
+        end
+      end
+
+      context "against a different string" do
+        it "is false" do
+          value = "foobar"
+          last = "baz"
+          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_false
+        end
+      end
+
+      context "against a matching character" do
+        it "is true" do
+          value = "foobar"
+          last = 'r'
+          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_true
+        end
+
+        context "not at end" do
+          it "is false" do
+            value = "foobar"
+            last = 'b'
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::EndWithMatcher.new(last)
+            matcher.match?(partial).should be_false
+          end
+        end
+      end
+
+      context "against a different character" do
+        it "is false" do
+          value = "foobar"
+          last = 'z'
+          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_false
+        end
+      end
+
+      context "against a matching regex" do
+        it "is true" do
+          value = "FOOBAR"
+          last = /bar/i
+          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_true
+        end
+
+        context "not at end" do
+          it "is false" do
+            value = "FOOBAR"
+            last = /foo/i
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::EndWithMatcher.new(last)
+            matcher.match?(partial).should be_false
+          end
+        end
+      end
+
+      context "against a non-matching regex" do
+        it "is false" do
+          value = "FOOBAR"
+          last = /baz/i
+          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_false
+        end
+      end
+    end
+
+    context "with an Enumberable" do
+      context "against an equal value" do
+        it "is true" do
+          array = %i[a b c]
+          last = :c
+          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_true
+        end
+
+        context "not at end" do
+          it "is false" do
+            array = %i[a b c]
+            last = :b
+            partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+            matcher = Spectator::Matchers::EndWithMatcher.new(last)
+            matcher.match?(partial).should be_false
+          end
+        end
+      end
+
+      context "against a different value" do
+        it "is false" do
+          array = %i[a b c]
+          last = :z
+          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_false
+        end
+      end
+
+      context "against matching element type" do
+        it "is true" do
+          array = %i[a b c]
+          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+          matcher = Spectator::Matchers::EndWithMatcher.new(Symbol)
+          matcher.match?(partial).should be_true
+        end
+
+        context "not at end" do
+          it "is false" do
+            array = [1, 2, 3, :a, :b, :c]
+            partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+            matcher = Spectator::Matchers::EndWithMatcher.new(Int32)
+            matcher.match?(partial).should be_false
+          end
+        end
+      end
+
+      context "against different element type" do
+        it "is false" do
+          array = %i[a b c]
+          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+          matcher = Spectator::Matchers::EndWithMatcher.new(Int32)
+          matcher.match?(partial).should be_false
+        end
+      end
+
+      context "against a matching regex" do
+        it "is true" do
+          array = %w[FOO BAR BAZ]
+          last = /baz/i
+          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_true
+        end
+
+        context "not at end" do
+          it "is false" do
+            array = %w[FOO BAR BAZ]
+            last = /bar/i
+            partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+            matcher = Spectator::Matchers::EndWithMatcher.new(last)
+            matcher.match?(partial).should be_false
+          end
+        end
+      end
+
+      context "against a non-matching regex" do
+        it "is false" do
+          array = %w[FOO BAR BAZ]
+          last = /qux/i
+          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+          matcher = Spectator::Matchers::EndWithMatcher.new(last)
+          matcher.match?(partial).should be_false
+        end
+      end
+    end
+  end
+
+  describe "#message" do
+    context "with a String" do
+      it "mentions #ends_with?" do
+        value = "foobar"
+        last = "baz"
+        partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+        matcher = Spectator::Matchers::EndWithMatcher.new(last)
+        matcher.message(partial).should contain("#starts_with?")
+      end
+    end
+
+    context "with an Enumerable" do
+      it "mentions ===" do
+        array = %i[a b c]
+        partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+        matcher = Spectator::Matchers::EndWithMatcher.new(array.last)
+        matcher.message(partial).should contain("===")
+      end
+    end
+
+    it "contains the actual label" do
+      value = "foobar"
+      last = "baz"
+      label = "everything"
+      partial = Spectator::Expectations::ValueExpectationPartial.new(label, value)
+      matcher = Spectator::Matchers::EndWithMatcher.new(last)
+      matcher.message(partial).should contain(label)
+    end
+
+    it "contains the expected label" do
+      value = "foobar"
+      last = "baz"
+      label = "everything"
+      partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+      matcher = Spectator::Matchers::EndWithMatcher.new(label, last)
+      matcher.message(partial).should contain(label)
+    end
+
+    context "when expected label is omitted" do
+      it "contains stringified form of expected value" do
+        value = "foobar"
+        last = "baz"
+        partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+        matcher = Spectator::Matchers::EndWithMatcher.new(last)
+        matcher.message(partial).should contain(last)
+      end
+    end
+  end
+
+  describe "#negated_message" do
+    context "with a String" do
+      it "mentions #starts_with?" do
+        value = "foobar"
+        last = "baz"
+        partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+        matcher = Spectator::Matchers::EndWithMatcher.new(last)
+        matcher.negated_message(partial).should contain("#starts_with?")
+      end
+    end
+
+    context "with an Enumerable" do
+      it "mentions ===" do
+        array = %i[a b c]
+        partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+        matcher = Spectator::Matchers::EndWithMatcher.new(array.last)
+        matcher.negated_message(partial).should contain("===")
+      end
+    end
+
+    it "contains the actual label" do
+      value = "foobar"
+      last = "baz"
+      label = "everything"
+      partial = Spectator::Expectations::ValueExpectationPartial.new(label, value)
+      matcher = Spectator::Matchers::EndWithMatcher.new(last)
+      matcher.negated_message(partial).should contain(label)
+    end
+
+    it "contains the expected label" do
+      value = "foobar"
+      last = "baz"
+      label = "everything"
+      partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+      matcher = Spectator::Matchers::EndWithMatcher.new(label, last)
+      matcher.negated_message(partial).should contain(label)
+    end
+
+    context "when expected label is omitted" do
+      it "contains stringified form of expected value" do
+        value = "foobar"
+        last = "baz"
+        partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+        matcher = Spectator::Matchers::EndWithMatcher.new(last)
+        matcher.negated_message(partial).should contain(last)
+      end
+    end
+  end
+end