diff --git a/third_party/blink/renderer/platform/fonts/mac/font_matcher_mac.mm b/third_party/blink/renderer/platform/fonts/mac/font_matcher_mac.mm
index 0b9c2ef..8d01704 100644
--- a/third_party/blink/renderer/platform/fonts/mac/font_matcher_mac.mm
+++ b/third_party/blink/renderer/platform/fonts/mac/font_matcher_mac.mm
@@ -194,16 +194,19 @@
   NSString* desired_family = desired_family_string;
   NSFontManager* font_manager = [NSFontManager sharedFontManager];
 
-  // Do a simple case insensitive search for a matching font family.
-  // NSFontManager requires exact name matches.
-  // This addresses the problem of matching arial to Arial, etc., but perhaps
-  // not all the issues.
-  NSEnumerator* e = [[font_manager availableFontFamilies] objectEnumerator];
-  NSString* available_family;
-  while ((available_family = [e nextObject])) {
-    if ([desired_family caseInsensitiveCompare:available_family] ==
-        NSOrderedSame)
-      break;
+  // From Mac OS 10.15 [NSFontManager availableFonts] does not list certain
+  // fonts that availableMembersOfFontFamily actually shows results for, for
+  // example "Hiragino Kaku Gothic ProN" is not listed, only Hiragino Sans is
+  // listed. We previously enumerated availableFontFamilies and looked for a
+  // case-insensitive string match here, but instead, we can rely on
+  // availableMembersOfFontFamily here to do a case-insensitive comparison, then
+  // set available_family to desired_family if the result was not empty.
+  // See https://crbug.com/1000542
+  NSString* available_family = nil;
+  NSArray* fonts_in_family =
+      [font_manager availableMembersOfFontFamily:desired_family];
+  if (fonts_in_family && [fonts_in_family count]) {
+    available_family = desired_family;
   }
 
   int app_kit_font_weight = ToAppKitFontWeight(desired_weight);
diff --git a/third_party/blink/web_tests/NeverFixTests b/third_party/blink/web_tests/NeverFixTests
index 192cde9..f2ea74f 100644
--- a/third_party/blink/web_tests/NeverFixTests
+++ b/third_party/blink/web_tests/NeverFixTests
@@ -144,6 +144,10 @@
 # Linux layout tests do not have a Myanmar fallback font.
 [ Linux ] inspector-protocol/layout-fonts/fallback-myanmar.js [ WontFix ]
 
+# Mac only test for case-insensitive font-matching.
+[ Linux ] inspector-protocol/layout-fonts/mac-case-insensitive-matching.js [ WontFix ]
+[ Win ] inspector-protocol/layout-fonts/mac-case-insensitive-matching.js [ WontFix ]
+
 # Segoe UI matching is only relevant on Windows
 [ Mac ] inspector-protocol/layout-fonts/font-weight-granularity-matching.js [ WontFix ]
 [ Linux ] inspector-protocol/layout-fonts/font-weight-granularity-matching.js [ WontFix ]
diff --git a/third_party/blink/web_tests/inspector-protocol/layout-fonts/mac-case-insensitive-matching.js b/third_party/blink/web_tests/inspector-protocol/layout-fonts/mac-case-insensitive-matching.js
new file mode 100644
index 0000000..ffee61a1
--- /dev/null
+++ b/third_party/blink/web_tests/inspector-protocol/layout-fonts/mac-case-insensitive-matching.js
@@ -0,0 +1,37 @@
+(async function(testRunner) {
+  var page = await testRunner.createPage();
+  await page.loadHTML(`
+    <html>
+    <meta charset="UTF-8">
+    <style>
+    </style>
+    <body>
+        <div class="test">
+            <!-- Use a different font size in order to avoid caching the FontDescriptions and skipping matching. -->
+            <div id="mixed_case_1" style="font-family: HIragINO KakU GothiC ProN; font-size: 12px;">クローミアム</div>
+            <div id="mixed_case_2" style="font-family: hiRAGino kAKu gOTHIc pROn; font-size: 13px;">クローミアム</div>
+            <div id="all_lower_case" style="font-family: hiragino kaku gothic pron; font-size: 14px;">クローミアム</div>
+            <div id="all_upper_case" style="font-family: HIRAGINO KAKU GOTHIC PRON; font-size: 15px;">クローミアム</div>
+            <div id="exact_case" style="font-family: Hiragino Kaku Gothic ProN; font-size: 16px;">クローミアム</div>
+        </div>
+    </body>
+    </html>
+  `);
+  var session = await page.createSession();
+  testRunner.log('Test passes if each of the test divs uses the Hiragino Kaku Gothic ProN ' +
+                 'independently of capitalization of the font family name..');
+
+  var helper = await testRunner.loadScript('./resources/layout-font-test.js');
+  var results = await helper(testRunner, session);
+
+  var passed = results.length == 5;
+  const reduce_match_regexp = (passed, currentValue) => {
+    var current_value_passes = /Hiragino Kaku Gothic ProN/.test(currentValue.usedFonts[0].familyName)
+        && currentValue.usedFonts[0].glyphCount == 6;
+    return passed && current_value_passes;
+  }
+  passed = passed && results.reduce(reduce_match_regexp);
+
+  testRunner.log(passed ? 'PASS' : 'FAIL');
+  testRunner.completeTest();
+})
diff --git a/third_party/blink/web_tests/platform/mac/inspector-protocol/layout-fonts/mac-case-insensitive-matching-expected.txt b/third_party/blink/web_tests/platform/mac/inspector-protocol/layout-fonts/mac-case-insensitive-matching-expected.txt
new file mode 100644
index 0000000..2fe13cd
--- /dev/null
+++ b/third_party/blink/web_tests/platform/mac/inspector-protocol/layout-fonts/mac-case-insensitive-matching-expected.txt
@@ -0,0 +1,23 @@
+Test passes if each of the test divs uses the Hiragino Kaku Gothic ProN independently of capitalization of the font family name..
+クローミアム
+#mixed_case_1:
+"Hiragino Kaku Gothic ProN" : 6
+
+クローミアム
+#mixed_case_2:
+"Hiragino Kaku Gothic ProN" : 6
+
+クローミアム
+#all_lower_case:
+"Hiragino Kaku Gothic ProN" : 6
+
+クローミアム
+#all_upper_case:
+"Hiragino Kaku Gothic ProN" : 6
+
+クローミアム
+#exact_case:
+"Hiragino Kaku Gothic ProN" : 6
+
+PASS
+