diff --git a/spring-test/src/test/java/org/springframework/test/web/client/match/ContentRequestMatchersTests.java b/spring-test/src/test/java/org/springframework/test/web/client/match/ContentRequestMatchersTests.java
index d4eef94bac..ee76368ab9 100644
--- a/spring-test/src/test/java/org/springframework/test/web/client/match/ContentRequestMatchersTests.java
+++ b/spring-test/src/test/java/org/springframework/test/web/client/match/ContentRequestMatchersTests.java
@@ -24,6 +24,7 @@ import org.junit.jupiter.api.Test;
 
 import org.springframework.http.MediaType;
 import org.springframework.mock.http.client.MockClientHttpRequest;
+import org.springframework.test.json.JsonCompareMode;
 import org.springframework.util.LinkedMultiValueMap;
 import org.springframework.util.MultiValueMap;
 
@@ -234,6 +235,16 @@ public class ContentRequestMatchersTests {
 
 		MockRestRequestMatchers.content().json("{\n \"foo array\":[\"second\",\"first\"] \n}")
 				.match(this.request);
+		MockRestRequestMatchers.content().json("{\n \"foo array\":[\"second\",\"first\"] \n}", JsonCompareMode.LENIENT)
+				.match(this.request);
+	}
+
+	@Test
+	@Deprecated
+	public void testJsonLenientMatchWithDeprecatedBooleanFlag() throws Exception {
+		String content = "{\n \"foo array\":[\"first\",\"second\"] , \"someExtraProperty\": \"which is allowed\" \n}";
+		this.request.getBody().write(content.getBytes());
+
 		MockRestRequestMatchers.content().json("{\n \"foo array\":[\"second\",\"first\"] \n}", false)
 				.match(this.request);
 	}
@@ -243,6 +254,18 @@ public class ContentRequestMatchersTests {
 		String content = "{\n \"foo\": \"bar\", \"foo array\":[\"first\",\"second\"] \n}";
 		this.request.getBody().write(content.getBytes());
 
+		MockRestRequestMatchers
+				.content()
+				.json("{\n \"foo array\":[\"first\",\"second\"] , \"foo\": \"bar\" \n}", JsonCompareMode.STRICT)
+				.match(this.request);
+	}
+
+	@Test
+	@Deprecated
+	public void testJsonStrictMatchWithDeprecatedBooleanFlag() throws Exception {
+		String content = "{\n \"foo\": \"bar\", \"foo array\":[\"first\",\"second\"] \n}";
+		this.request.getBody().write(content.getBytes());
+
 		MockRestRequestMatchers
 				.content()
 				.json("{\n \"foo array\":[\"first\",\"second\"] , \"foo\": \"bar\" \n}", true)
@@ -259,6 +282,19 @@ public class ContentRequestMatchersTests {
 						.content()
 						.json("{\n \"foo\" : \"bar\"  \n}")
 						.match(this.request));
+		assertThatExceptionOfType(AssertionError.class).isThrownBy(() ->
+				MockRestRequestMatchers
+						.content()
+						.json("{\n \"foo\" : \"bar\"  \n}", JsonCompareMode.LENIENT)
+						.match(this.request));
+	}
+
+	@Test
+	@Deprecated
+	public void testJsonLenientNoMatchWithDeprecatedBooleanFlag() throws Exception {
+		String content = "{\n \"bar\" : \"foo\"  \n}";
+		this.request.getBody().write(content.getBytes());
+
 		assertThatExceptionOfType(AssertionError.class).isThrownBy(() ->
 				MockRestRequestMatchers
 						.content()
@@ -271,6 +307,19 @@ public class ContentRequestMatchersTests {
 		String content = "{\n \"foo array\":[\"first\",\"second\"] , \"someExtraProperty\": \"which is NOT allowed\" \n}";
 		this.request.getBody().write(content.getBytes());
 
+		assertThatExceptionOfType(AssertionError.class).isThrownBy(() ->
+				MockRestRequestMatchers
+						.content()
+						.json("{\n \"foo array\":[\"second\",\"first\"] \n}", JsonCompareMode.STRICT)
+						.match(this.request));
+	}
+
+	@Test
+	@Deprecated
+	public void testJsonStrictNoMatchWithDeprecatedBooleanFlag() throws Exception {
+		String content = "{\n \"foo array\":[\"first\",\"second\"] , \"someExtraProperty\": \"which is NOT allowed\" \n}";
+		this.request.getBody().write(content.getBytes());
+
 		assertThatExceptionOfType(AssertionError.class).isThrownBy(() ->
 				MockRestRequestMatchers
 						.content()
diff --git a/spring-test/src/test/java/org/springframework/test/web/servlet/result/ContentResultMatchersTests.java b/spring-test/src/test/java/org/springframework/test/web/servlet/result/ContentResultMatchersTests.java
index fa98d3d1ea..4c28ae7fb9 100644
--- a/spring-test/src/test/java/org/springframework/test/web/servlet/result/ContentResultMatchersTests.java
+++ b/spring-test/src/test/java/org/springframework/test/web/servlet/result/ContentResultMatchersTests.java
@@ -20,6 +20,7 @@ import org.hamcrest.Matchers;
 import org.junit.jupiter.api.Test;
 
 import org.springframework.mock.web.MockHttpServletResponse;
+import org.springframework.test.json.JsonCompareMode;
 import org.springframework.test.web.servlet.StubMvcResult;
 
 import static java.nio.charset.StandardCharsets.UTF_8;
@@ -80,13 +81,31 @@ class ContentResultMatchersTests {
 	@Test
 	void jsonLenientMatch() throws Exception {
 		new ContentResultMatchers().json("{\n \"foo\" : \"bar\"  \n}").match(getStubMvcResult(CONTENT));
+		new ContentResultMatchers().json("{\n \"foo\" : \"bar\"  \n}",
+				JsonCompareMode.LENIENT).match(getStubMvcResult(CONTENT));
+	}
+
+	@Test
+	@Deprecated
+	void jsonLenientMatchWithDeprecatedBooleanFlag() throws Exception {
 		new ContentResultMatchers().json("{\n \"foo\" : \"bar\"  \n}", false).match(getStubMvcResult(CONTENT));
 	}
 
 	@Test
 	void jsonStrictMatch() throws Exception {
-		new ContentResultMatchers().json("{\n \"foo\":\"bar\",   \"foo array\":[\"foo\",\"bar\"] \n}", true).match(getStubMvcResult(CONTENT));
-		new ContentResultMatchers().json("{\n \"foo array\":[\"foo\",\"bar\"], \"foo\":\"bar\" \n}", true).match(getStubMvcResult(CONTENT));
+		new ContentResultMatchers().json("{\n \"foo\":\"bar\",   \"foo array\":[\"foo\",\"bar\"] \n}",
+				JsonCompareMode.STRICT).match(getStubMvcResult(CONTENT));
+		new ContentResultMatchers().json("{\n \"foo array\":[\"foo\",\"bar\"], \"foo\":\"bar\" \n}",
+				JsonCompareMode.STRICT).match(getStubMvcResult(CONTENT));
+	}
+
+	@Test
+	@Deprecated
+	void jsonStrictMatchWithDeprecatedBooleanFlag() throws Exception {
+		new ContentResultMatchers().json("{\n \"foo\":\"bar\",   \"foo array\":[\"foo\",\"bar\"] \n}", true)
+				.match(getStubMvcResult(CONTENT));
+		new ContentResultMatchers().json("{\n \"foo array\":[\"foo\",\"bar\"], \"foo\":\"bar\" \n}", true)
+				.match(getStubMvcResult(CONTENT));
 	}
 
 	@Test
@@ -98,7 +117,16 @@ class ContentResultMatchersTests {
 	@Test
 	void jsonStrictNoMatch() {
 		assertThatExceptionOfType(AssertionError.class).isThrownBy(() ->
-				new ContentResultMatchers().json("{\"foo\":\"bar\",   \"foo array\":[\"bar\",\"foo\"]}", true).match(getStubMvcResult(CONTENT)));
+				new ContentResultMatchers().json("{\"foo\":\"bar\",   \"foo array\":[\"bar\",\"foo\"]}",
+						JsonCompareMode.STRICT).match(getStubMvcResult(CONTENT)));
+	}
+
+	@Test
+	@Deprecated
+	void jsonStrictNoMatchWithDeprecatedBooleanFlag() {
+		assertThatExceptionOfType(AssertionError.class).isThrownBy(() ->
+				new ContentResultMatchers().json("{\"foo\":\"bar\",   \"foo array\":[\"bar\",\"foo\"]}", true)
+						.match(getStubMvcResult(CONTENT)));
 	}
 
 	@Test  // gh-23622