diff --git a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy
index b1bb570bf3..f1b0c532ff 100644
--- a/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy
+++ b/spring-cloud-contract-verifier/src/main/groovy/org/springframework/cloud/contract/verifier/util/ContentUtils.groovy
@@ -39,6 +39,7 @@ import org.springframework.cloud.contract.spec.internal.MatchingStrategy
 import org.springframework.cloud.contract.spec.internal.NamedProperty
 import org.springframework.cloud.contract.spec.internal.OptionalProperty
 import org.springframework.cloud.contract.verifier.template.HandlebarsTemplateProcessor
+import org.springframework.util.StringUtils
 
 import static org.apache.commons.text.StringEscapeUtils.escapeJava
 import static org.apache.commons.text.StringEscapeUtils.escapeJson
@@ -108,7 +109,7 @@ class ContentUtils {
 	 * @return JSON structure with replaced client / server side parts
 	 */
 	static Object extractValue(GString bodyAsValue, ContentType contentType, Closure valueProvider) {
-		if (bodyAsValue.isEmpty()) {
+		if (!StringUtils.hasText(bodyAsValue.toString())) {
 			return bodyAsValue
 		}
 		if (contentType == ContentType.TEXT || contentType == ContentType.FORM) {
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 8113c1333b..7782fd61a2 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
@@ -140,7 +140,7 @@ class JsonToJsonPathsConverter {
 	}
 
 	/**
-	 * Related to #391 and #1091. The converted body looks different when done via the String notation than
+	 * Related to #391 and #1091 and #1414. 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
 	 * are provided, even when all entries of a map / list got removed, the map / list itself
 	 * remains. That leads to unnecessary creation of checks for empty collection. With this method
@@ -163,8 +163,16 @@ class JsonToJsonPathsConverter {
 					&& isNotRootArray(matcherPath)) {
 				String pathToDelete = pathToDelete(pathWithoutAnyArray)
 				context.delete(pathToDelete)
-				return pathToDelete.contains(DESCENDANT_OPERATOR) ? false :
-						removeTrailingContainers(pathToDelete, context)
+				if (pathToDelete.contains(DESCENDANT_OPERATOR)) {
+					Object root = context.read('$')
+					if (rootContainsEmptyContainers(root)) {
+						// now root contains only empty elements, we should remove the trailing containers
+						context.delete('$[*]')
+						return false
+					}
+					return false
+				}
+				return removeTrailingContainers(pathToDelete, context)
 			}
 			else {
 				int lastIndexOfDot = matcherPath.lastIndexOf(".")
@@ -191,6 +199,10 @@ class JsonToJsonPathsConverter {
 		}
 	}
 
+	private static boolean rootContainsEmptyContainers(root) {
+		root instanceof Iterable && root.every { containsOnlyEmptyElements(it) }
+	}
+
 	private static String lastMatch(Matcher matcher) {
 		List<String> matches = []
 		while ({
@@ -204,6 +216,10 @@ class JsonToJsonPathsConverter {
 		return object instanceof Iterable || object instanceof Map
 	}
 
+	private static boolean isEmpty(Object object) {
+		return isIterable(object) && object instanceof Iterable ? object.isEmpty() : ((Map) object).isEmpty()
+	}
+
 	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 66954c7d80..9be94f1cdd 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
@@ -1755,6 +1755,65 @@ response:
 			}
 	}
 
+	@Issue("#1414")
+	def "should work with empty arrays after doing array matching [#methodBuilderName]"() {
+		given:
+			String yaml = '''\
+name: GET sample
+description: sample
+request:
+  method: GET
+  urlPath: /sample
+response:
+  status: 200
+  body:
+    - foo: "sample1"
+      bar: true
+    - foo: "sample2"
+      bar: false
+  headers:
+    Content-Type: application/json
+  matchers:
+    body:
+      - path: $..foo
+        type: by_regex
+        value: .*
+      - path: $..bar
+        type: by_regex
+        predefined: any_boolean
+'''
+			File tmpFile = File.createTempFile("foo", ".yml")
+			tmpFile.createNewFile()
+			tmpFile.text = yaml
+			Contract contractDsl = new YamlContractConverter().convertFrom(tmpFile).
+					first()
+			methodBuilder()
+		when:
+			String test = singleTestGenerator(contractDsl)
+		then:
+			SyntaxChecker.tryToCompileWithoutCompileStatic(methodBuilderName, test)
+			!test.contains('''assertThatJson(parsedJson).array().isEmpty()''')
+		and:
+			stubMappingIsValidWireMockStub(contractDsl)
+		where:
+			methodBuilderName | methodBuilder
+			"spock"           | {
+				properties.testFramework = TestFramework.SPOCK
+			}
+			"mockmvc"         | {
+				properties.testMode = TestMode.MOCKMVC
+			}
+			"jaxrs-spock"     | {
+				properties.testFramework = TestFramework.SPOCK; properties.testMode = TestMode.JAXRSCLIENT
+			}
+			"jaxrs"           | {
+				properties.testFramework = TestFramework.JUNIT; properties.testMode = TestMode.JAXRSCLIENT
+			}
+			"testNG"          | {
+				properties.testFramework = TestFramework.TESTNG
+			}
+	}
+
 	@Issue("#1262")
 	def "should work with the timeout flag for groovy [#methodBuilderName]"() {
 		given: