diff --git a/src/vs/workbench/services/themes/common/colorThemeData.ts b/src/vs/workbench/services/themes/common/colorThemeData.ts
index ca5fb5e9e3d58d29ab0c7c5ddde82db17307cd0b..bacaa95f9f7a5a07063df3f847a2891bcac2b01a 100644
--- a/src/vs/workbench/services/themes/common/colorThemeData.ts
+++ b/src/vs/workbench/services/themes/common/colorThemeData.ts
@@ -293,9 +293,11 @@ export class ColorThemeData implements IWorkbenchColorTheme {
 						const settings = tokenColors[i].settings;
 						if (score >= foregroundScore && settings.foreground) {
 							foreground = settings.foreground;
+							foregroundScore = score;
 						}
 						if (score >= fontStyleScore && types.isString(settings.fontStyle)) {
 							fontStyle = settings.fontStyle;
+							fontStyleScore = score;
 						}
 					}
 				}
@@ -657,7 +659,7 @@ function nameMatcher(identifers: string[], scope: ProbeScope): number {
 	let lastScopeIndex = scope.length - 1;
 	let lastIdentifierIndex = findInIdents(scope[lastScopeIndex--], identifers.length);
 	if (lastIdentifierIndex >= 0) {
-		const score = (lastIdentifierIndex + 1) * 0x10000 + scope.length;
+		const score = (lastIdentifierIndex + 1) * 0x10000 + identifers[lastIdentifierIndex].length;
 		while (lastScopeIndex >= 0) {
 			lastIdentifierIndex = findInIdents(scope[lastScopeIndex--], lastIdentifierIndex);
 			if (lastIdentifierIndex === -1) {
diff --git a/src/vs/workbench/services/themes/test/electron-browser/tokenStyleResolving.test.ts b/src/vs/workbench/services/themes/test/electron-browser/tokenStyleResolving.test.ts
index 8f5da0882882e3d1f37a1e6db60204cb63d37dcb..242182ce537291e0921fdd22254c35257ec09238 100644
--- a/src/vs/workbench/services/themes/test/electron-browser/tokenStyleResolving.test.ts
+++ b/src/vs/workbench/services/themes/test/electron-browser/tokenStyleResolving.test.ts
@@ -289,6 +289,41 @@ suite('Themes - TokenStyleResolving', () => {
 
 	});
 
+
+	test('resolveScopes - match most specific', async () => {
+		const themeData = ColorThemeData.createLoadedEmptyTheme('test', 'test');
+
+		const customTokenColors: ITokenColorCustomizations = {
+			textMateRules: [
+				{
+					scope: 'entity.name.type',
+					settings: {
+						fontStyle: 'underline',
+						foreground: '#A6E22E'
+					}
+				},
+				{
+					scope: 'entity.name.type.class',
+					settings: {
+						foreground: '#FF00FF'
+					}
+				},
+				{
+					scope: 'entity.name',
+					settings: {
+						foreground: '#FFFFFF'
+					}
+				},
+			]
+		};
+
+		themeData.setCustomTokenColors(customTokenColors);
+
+		const tokenStyle = themeData.resolveScopes([['entity.name.type.class']]);
+		assertTokenStyle(tokenStyle, ts('#FF00FF', { underline: true }), 'entity.name.type.class');
+
+	});
+
 	test('rule matching', async () => {
 		const themeData = ColorThemeData.createLoadedEmptyTheme('test', 'test');
 		themeData.setCustomColors({ 'editor.foreground': '#000000' });