diff --git a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy
index b602f3bc23..e87c5c59f5 100644
--- a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy
+++ b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/JsonToJsonPathsConverter.groovy
@@ -84,8 +84,11 @@ class JsonToJsonPathsConverter {
 		if (bodyMatchers?.hasMatchers()) {
 			bodyMatchers.jsonPathMatchers().each { BodyMatcher matcher ->
 				try {
-					context.delete(matcher.path())
-					removeTrailingContainers(matcher, context)
+					def entry = entry(context, matcher.path())
+					if (entry != null) {
+						context.delete(matcher.path())
+						removeTrailingContainers(matcher, context)
+					}
 				} catch (RuntimeException e) {
 					if (log.isDebugEnabled()) {
 						log.debug("Exception occurred while trying to delete path [${matcher.path()}]", e)
@@ -96,6 +99,17 @@ class JsonToJsonPathsConverter {
 		return jsonCopy
 	}
 
+	private static def entry(DocumentContext context, String path) {
+		try {
+			return context.read(path)
+		} catch (Exception ex) {
+			if (log.isDebugEnabled()) {
+				log.debug("Exception occurred while trying to retrieve element via path [${path}]", ex)
+			}
+			return null
+		}
+	}
+
 	/**
 	 * Related to #391. The converted body looks different when done via the String notation than
 	 * it does when done via a map notation. When working with String body and when matchers
@@ -106,22 +120,26 @@ class JsonToJsonPathsConverter {
 	 * defining body...
 	 */
 	private static void removeTrailingContainers(BodyMatcher matcher, DocumentContext context) {
-		if (matcher.path().contains(ANY_ARRAY_NOTATION_IN_JSONPATH)) {
-			String pathWithoutAnyArray = matcher.path().substring(0, matcher.path().lastIndexOf(ANY_ARRAY_NOTATION_IN_JSONPATH))
-			def object = context.read(pathWithoutAnyArray)
-			if (object instanceof Iterable && containsOnlyEmptyElements(object)) {
-				String pathToDelete = pathToDelete(pathWithoutAnyArray)
-				context.delete(pathToDelete)
-			} else {
-				String lastParent = matcher.path().substring(0, matcher.path().lastIndexOf("."))
-				def lastParentObject = context.read(lastParent)
-				if (lastParentObject instanceof Iterable && containsOnlyEmptyElements(lastParentObject)) {
-					context.delete(lastParent)
-				}
+		String pathWithoutAnyArray = matcher.path().contains(ANY_ARRAY_NOTATION_IN_JSONPATH) ? matcher.path().substring(0, matcher.path().lastIndexOf(ANY_ARRAY_NOTATION_IN_JSONPATH)) : matcher.path()
+		def object = entry(context, pathWithoutAnyArray)
+		// object got removed and it was the only element
+		// let's get its parent and see if it contains an empty element
+		if (isIterable(object) && containsOnlyEmptyElements(object)) {
+			String pathToDelete = pathToDelete(pathWithoutAnyArray)
+			context.delete(pathToDelete)
+		} else {
+			String lastParent = matcher.path().substring(0, matcher.path().lastIndexOf("."))
+			def lastParentObject = context.read(lastParent)
+			if (isIterable(lastParentObject) && containsOnlyEmptyElements(lastParentObject)) {
+				context.delete(lastParent)
 			}
 		}
 	}
 
+	private static boolean isIterable(Object object) {
+		return object instanceof Iterable || object instanceof Map
+	}
+
 	private static String pathToDelete(String pathWithoutAnyArray) {
 		// we can't remove root
 		return pathWithoutAnyArray == '$' ? '$[*]' : pathWithoutAnyArray
diff --git a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy
index 81a292e711..248b3ecb01 100644
--- a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy
+++ b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/builder/MethodBodyBuilderSpec.groovy
@@ -981,4 +981,49 @@ DocumentContext parsedJson = JsonPath.parse(json);
 			"JaxRsClientJUnitMethodBodyBuilder"                  | { Contract dsl -> new JaxRsClientJUnitMethodBodyBuilder(dsl, properties) }
 	}
 
+	@Issue("#727")
+	def "should not leave empty arrays [#methodBuilderName]"() {
+		given:
+			Contract contractDsl = Contract.make {
+				request {
+					method 'GET'
+					url '/list'
+				}
+				response {
+					status 200
+					body(
+							[
+									content: [
+											one: "two",
+											two: "two",
+											three: [
+													six: "seven"
+											]
+									]
+							]
+					)
+					bodyMatchers {
+						jsonPath('$.content.three.six', byRegex(".*seven.*"))
+						jsonPath('$.content.one', byRegex(".*two.*"))
+					}
+				}
+			}
+			MethodBodyBuilder builder = methodBuilder(contractDsl)
+			BlockBuilder blockBuilder = new BlockBuilder(" ")
+		when:
+			builder.appendTo(blockBuilder)
+		then:
+			String test = blockBuilder.toString()
+			SyntaxChecker.tryToCompileWithoutCompileStatic(methodBuilderName, test)
+			!test.contains('''.isEmpty()''')
+		and:
+			stubMappingIsValidWireMockStub(contractDsl)
+		where:
+			methodBuilderName                                    | methodBuilder
+			"MockMvcSpockMethodBuilder"                          | { Contract dsl -> new MockMvcSpockMethodRequestProcessingBodyBuilder(dsl, properties) }
+			"MockMvcJUnitMethodBuilder"                          | { Contract dsl -> new MockMvcJUnitMethodBodyBuilder(dsl, properties) }
+			"JaxRsClientSpockMethodRequestProcessingBodyBuilder" | { Contract dsl -> new JaxRsClientSpockMethodRequestProcessingBodyBuilder(dsl, properties) }
+			"JaxRsClientJUnitMethodBodyBuilder"                  | { Contract dsl -> new JaxRsClientJUnitMethodBodyBuilder(dsl, properties) }
+	}
+
 }