diff --git a/src/vs/base/common/filters.ts b/src/vs/base/common/filters.ts
index 688488529f26b..ed5d856458528 100644
--- a/src/vs/base/common/filters.ts
+++ b/src/vs/base/common/filters.ts
@@ -577,21 +577,20 @@ export function fuzzyScore(pattern: string, word: string): [number, number[]] {
 
 function findAllMatches(patternLen: number, patternPos: number, wordPos: number, total: number, matches: number[], bucket: [number, number[]][]): void {
 
+	let lastMatched = false;
+
 	while (patternPos > 0 && wordPos > 0) {
-		let value = _table[patternPos][wordPos];
+
 		let score = _scores[patternPos][wordPos];
 		let arrow = _arrows[patternPos][wordPos];
 
 		if (arrow === Arrow.Left || score < 0) {
 			// left
 			wordPos -= 1;
-
-		} else if (arrow === Arrow.Diag) {
-			// diag
-			total += value;
-			patternPos -= 1;
-			wordPos -= 1;
-			matches.unshift(wordPos);
+			if (lastMatched) {
+				total -= 5; // gap penalty
+			}
+			lastMatched = false;
 
 		} else if (arrow & Arrow.Diag) {
 
@@ -601,10 +600,11 @@ function findAllMatches(patternLen: number, patternPos: number, wordPos: number,
 			}
 
 			// diag
-			total += value;
+			total += score;
 			patternPos -= 1;
 			wordPos -= 1;
 			matches.unshift(wordPos);
+			lastMatched = true;
 
 		} else {
 			return undefined;
diff --git a/src/vs/base/test/common/filters.test.ts b/src/vs/base/test/common/filters.test.ts
index e1fd42d7d72f5..15f8433add393 100644
--- a/src/vs/base/test/common/filters.test.ts
+++ b/src/vs/base/test/common/filters.test.ts
@@ -224,6 +224,13 @@ suite('Filters', () => {
 		assertMatches('c:\\do', '& \'c:\\Documents and Settings\'', '& \'^c^:^\\^D^ocuments and Settings\'', fuzzyScore);
 	});
 
+	test('fuzzyScore, #23581', function () {
+		assertMatches('close', 'css.lint.importStatement', '^css.^lint.imp^ort^Stat^ement', fuzzyScore);
+		assertMatches('close', 'css.colorDecorators.enable', '^css.co^l^orDecorator^s.^enable', fuzzyScore);
+		assertMatches('close', 'workbench.quickOpen.closeOnFocusOut', 'workbench.quickOpen.^c^l^o^s^eOnFocusOut', fuzzyScore);
+		assertTopScore(fuzzyScore, 'close', 2, 'css.lint.importStatement', 'css.colorDecorators.enable', 'workbench.quickOpen.closeOnFocusOut');
+	});
+
 	test('fuzzyScore', function () {
 		assertMatches('ab', 'abA', '^a^bA', fuzzyScore);
 		assertMatches('ccm', 'cacmelCase', '^ca^c^melCase', fuzzyScore);
@@ -277,7 +284,7 @@ suite('Filters', () => {
 
 	});
 	function assertTopScore(filter: typeof fuzzyScore, pattern: string, expected: number, ...words: string[]) {
-		let topScore = -Number.MIN_VALUE;
+		let topScore = -(100 * 10);
 		let topIdx = 0;
 		for (let i = 0; i < words.length; i++) {
 			const word = words[i];
diff --git a/src/vs/editor/contrib/suggest/common/completionModel.ts b/src/vs/editor/contrib/suggest/common/completionModel.ts
index 70e4908c0c9e5..b611b449e5aa6 100644
--- a/src/vs/editor/contrib/suggest/common/completionModel.ts
+++ b/src/vs/editor/contrib/suggest/common/completionModel.ts
@@ -105,7 +105,7 @@ export class CompletionModel {
 
 		const { leadingLineContent, characterCountDelta } = this._lineContext;
 		let word = '';
-		let topScore = -Number.MIN_VALUE;
+		let topScore = -(100 * 10);
 
 		for (const item of this._items) {