diff --git a/hamcrest/src/main/java/org/hamcrest/collection/IsIterableContainingInAnyOrder.java b/hamcrest/src/main/java/org/hamcrest/collection/IsIterableContainingInAnyOrder.java
index 262a1263..7af9ecce 100644
--- a/hamcrest/src/main/java/org/hamcrest/collection/IsIterableContainingInAnyOrder.java
+++ b/hamcrest/src/main/java/org/hamcrest/collection/IsIterableContainingInAnyOrder.java
@@ -3,11 +3,9 @@
 import org.hamcrest.Description;
 import org.hamcrest.Matcher;
 import org.hamcrest.TypeSafeDiagnosingMatcher;
+import org.hamcrest.comparator.ComparatorMatcherBuilder;
 
-import java.util.ArrayList;
-import java.util.Arrays;
-import java.util.Collection;
-import java.util.List;
+import java.util.*;
 
 import static org.hamcrest.core.IsEqual.equalTo;
 
@@ -138,6 +136,42 @@ public static <T> Matcher<Iterable<? extends T>> containsInAnyOrder(T... items)
         return new IsIterableContainingInAnyOrder<>(matchers);
     }
 
+    /**
+     * <p>
+     * Creates an order agnostic matcher for {@link Iterable}s that matches when a single pass over
+     * the examined {@link Iterable} yields a series of items, each logically equal according to
+     * the comparator to one item anywhere in the specified items. For a positive match, the
+     * examined iterable must be of the same length as the number of specified items.
+     * </p>
+     * <p>
+     * N.B. each of the specified items will only be used once during a given examination, so be
+     * careful when specifying items that may be equal to more than one entry in an examined
+     * iterable.
+     * </p>
+     * <p>
+     * For example:
+     * </p>
+     * <pre>assertThat(Arrays.asList("first", "second"), containsInAnyOrder(new StringLengthComparator(), "abcde", "ZYXWVU"))</pre>
+     *
+     * @param <T>
+     *     the matcher type.
+     * @param comparator
+     *     the comparator to use to compare items to the items provided.
+     * @param items
+     *     the items that must equal (according to the provided comparator) the items provided by
+     *     an examined {@link Iterable} in any order
+     * @return The matcher.
+     */
+    @SafeVarargs
+    public static <T> Matcher<Iterable<? extends T>> containsInAnyOrder(Comparator<T> comparator, T... items) {
+        List<Matcher<? super T>> matchers = new ArrayList<>();
+        for (T item : items) {
+            matchers.add(ComparatorMatcherBuilder.comparedBy(comparator).comparesEqualTo(item));
+        }
+
+        return containsInAnyOrder(matchers);
+    }
+
     /**
      * <p>
      * Creates an order agnostic matcher for {@link Iterable}s that matches when a single pass over
diff --git a/hamcrest/src/test/java/org/hamcrest/collection/IsIterableContainingInAnyOrderTest.java b/hamcrest/src/test/java/org/hamcrest/collection/IsIterableContainingInAnyOrderTest.java
index d27ff3ff..f29e1334 100644
--- a/hamcrest/src/test/java/org/hamcrest/collection/IsIterableContainingInAnyOrderTest.java
+++ b/hamcrest/src/test/java/org/hamcrest/collection/IsIterableContainingInAnyOrderTest.java
@@ -5,11 +5,15 @@
 import org.hamcrest.collection.IsIterableContainingInOrderTest.WithValue;
 
 import java.util.Collections;
+import java.util.Comparator;
+import java.util.List;
+import java.util.Objects;
 
 import static java.util.Arrays.asList;
 import static org.hamcrest.collection.IsIterableContainingInAnyOrder.containsInAnyOrder;
 import static org.hamcrest.collection.IsIterableContainingInOrderTest.make;
 import static org.hamcrest.collection.IsIterableContainingInOrderTest.value;
+import static org.hamcrest.collection.IsIterableContainingInAnyOrderTest.Item.item;
 
 public class IsIterableContainingInAnyOrderTest extends AbstractMatcherTest {
 
@@ -52,4 +56,98 @@ public void testHasAReadableDescription() {
         assertDescription("iterable with items [<1>, <2>] in any order", containsInAnyOrder(1, 2));
     }
 
+    private static final ItemValueComparator comparator = new ItemValueComparator();
+
+    private static class ItemValueComparator implements Comparator<Item> {
+        @Override
+        public int compare(Item o1, Item o2) {
+            return Integer.compare(o1.value, o2.value);
+        }
+
+        @Override
+        public String toString() {
+            return ItemValueComparator.class.getSimpleName();
+        }
+    }
+
+    public static class Item {
+        private final String key;
+        private final int value;
+
+        private Item(String key, int value) {
+            this.key = key;
+            this.value = value;
+        }
+
+        public static Item item(String key, int value) {
+            return new Item(key, value);
+        }
+
+        public int getValue() {
+            return value;
+        }
+
+        @Override
+        public String toString() {
+            return key + ":" + value;
+        }
+
+        @Override
+        public boolean equals(Object o) {
+            if (this == o) return true;
+            if (o == null || getClass() != o.getClass()) return false;
+            Item item = (Item) o;
+            return Objects.equals(key, item.key);
+        }
+
+        @Override
+        public int hashCode() {
+            return Objects.hash(key);
+        }
+    }
+
+    public void testMatchesSingleItemIterableWithComparator() {
+        assertMatches("single item", containsInAnyOrder(comparator, item("key", 1)), Collections.singletonList(item("foo", 1)));
+    }
+
+    public void testDoesNotMatchEmptyWithComparator() {
+        List<Integer> actual = Collections.<Integer>emptyList();
+        Matcher<Iterable<? extends Item>> expected = containsInAnyOrder(comparator, item("key", 5), item("key", 10));
+        assertMismatchDescription("no item matches: a value equal to <key:5> when compared by <ItemValueComparator>, a value equal to <key:10> when compared by <ItemValueComparator> in []", expected, actual);
+    }
+
+    public void testMatchesIterableOutOfOrderWithComparator() {
+        List<Item> actual = asList(item("foo", 2), item("bar", 1));
+        Matcher<Iterable<? extends Item>> expected = containsInAnyOrder(comparator, item("key", 1), item("key", 2));
+        assertMatches("Out of order", expected, actual);
+    }
+
+    public void testMatchesIterableInOrderWithComparator() {
+        List<Item> actual = asList(item("foo", 1), item("bar", 2));
+        Matcher<Iterable<? extends Item>> expected = containsInAnyOrder(comparator, item("key", 1), item("key", 2));
+        assertMatches("In order", expected, actual);
+    }
+
+    public void testDoesNotMatchIfOneOfMultipleElementsMismatchesWithComparator() {
+        List<Item> actual = asList(item("foo", 1), item("bar", 2), item("baz", 4));
+        Matcher<Iterable<? extends Item>> expected = containsInAnyOrder(comparator, item("key", 1), item("key", 2), item("key", 3));
+        assertMismatchDescription("not matched: <baz:4>", expected, actual);
+    }
+
+    public void testDoesNotMatchIfThereAreMoreElementsThanMatchersWithComparator() {
+        List<Item> actual = asList(item("foo", 1), item("bar", 2), item("baz", 3));
+        final Matcher<Iterable<? extends Item>> expected = containsInAnyOrder(comparator, item("key", 1), item("key", 3));
+        assertMismatchDescription("not matched: <bar:2>", expected, actual);
+    }
+
+    public void testDoesNotMatchIfThereAreMoreMatchersThanElementsWithComparator() {
+        List<Item> actual = asList(item("foo", 1), item("bar", 2));
+        Matcher<Iterable<? extends Item>> expected = containsInAnyOrder(comparator, item("key", 1), item("key", 2), item("key", 3));
+        assertMismatchDescription("no item matches: a value equal to <key:3> when compared by <ItemValueComparator> in [<foo:1>, <bar:2>]", expected, actual);
+    }
+
+    public void testHasAReadableDescriptionWithComparator() {
+        assertDescription("iterable with items [a value equal to <foo:1> when compared by <ItemValueComparator>, a value equal to <bar:2> when compared by <ItemValueComparator>] in any order",
+            containsInAnyOrder(comparator, item("foo", 1), item("bar", 2)));
+    }
 }