diff --git a/‎packages/eslint-plugin/rules/type-annotation-spacing/type-annotation-spacing.test.ts‎
Lines changed: 9 additions & 0 deletions b/‎packages/eslint-plugin/rules/type-annotation-spacing/type-annotation-spacing.test.ts‎
Lines changed: 9 additions & 0 deletions
diff --git a/‎packages/eslint-plugin/rules/type-annotation-spacing/type-annotation-spacing.ts‎
Lines changed: 14 additions & 13 deletions b/‎packages/eslint-plugin/rules/type-annotation-spacing/type-annotation-spacing.ts‎
Lines changed: 14 additions & 13 deletions
@@ -1171,6 +1171,8 @@ interface Foo {
     },
     // https://github.com/typescript-eslint/typescript-eslint/issues/1663
     'type ConstructorFn = new (...args: any[]) => any;',
+    // https://github.com/eslint-stylistic/eslint-stylistic/issues/441
+    `function error_is_reported_ok(): (void) {}`,
   ],
   invalid: [
     {
@@ -3786,6 +3788,13 @@ type Foo = {
         },
       ],
     },
+    {
+      code: `function error_is_reported_ok():(void) {}`,
+      output: `function error_is_reported_ok(): (void) {}`,
+      errors: [
+        { messageId: 'expectedSpaceAfter', data: { type: ':' }, line: 1, column: 32 },
+      ],
+    },
   ],
 })
 
 
@@ -1,4 +1,5 @@
 import type { ASTNode, Tree } from '#types'
+import { isNotOpeningParenToken } from '#utils/ast'
 import { createRule } from '#utils/create-rule'
 
 import {
@@ -165,8 +166,9 @@ export default createRule<Options, MessageIds>({
     function checkTypeAnnotationSpacing(
       typeAnnotation: Tree.TypeNode,
     ): void {
-      const nextNode = typeAnnotation
-      const punctuatorTokenEnd = sourceCode.getTokenBefore(nextNode)!
+      /** :, => */
+      const punctuatorTokenEnd = sourceCode.getTokenBefore(typeAnnotation, isNotOpeningParenToken)!
+      /** :, =>, ?() */
       let punctuatorTokenStart = punctuatorTokenEnd
       let previousToken = sourceCode.getTokenBefore(punctuatorTokenEnd)!
       let type = punctuatorTokenEnd.value
@@ -177,9 +179,8 @@ export default createRule<Options, MessageIds>({
       const { before, after } = getRules(ruleSet, typeAnnotation)
 
       if (type === ':' && previousToken.value === '?') {
-        if (
-          sourceCode.isSpaceBetween(previousToken, punctuatorTokenStart)
-        ) {
+        // space between ? and :
+        if (sourceCode.isSpaceBetween(previousToken, punctuatorTokenStart)) {
           context.report({
             node: punctuatorTokenStart,
             messageId: 'unexpectedSpaceBetween',
@@ -209,11 +210,9 @@ export default createRule<Options, MessageIds>({
         }
       }
 
-      const previousDelta
-        = punctuatorTokenStart.range[0] - previousToken.range[1]
-      const nextDelta = nextNode.range[0] - punctuatorTokenEnd.range[1]
+      const hasNextSpace = sourceCode.isSpaceBetween(punctuatorTokenEnd, typeAnnotation)
 
-      if (after && nextDelta === 0) {
+      if (after && !hasNextSpace) {
         context.report({
           node: punctuatorTokenEnd,
           messageId: 'expectedSpaceAfter',
@@ -225,7 +224,7 @@ export default createRule<Options, MessageIds>({
           },
         })
       }
-      else if (!after && nextDelta > 0) {
+      else if (!after && hasNextSpace) {
         context.report({
           node: punctuatorTokenEnd,
           messageId: 'unexpectedSpaceAfter',
@@ -235,13 +234,15 @@ export default createRule<Options, MessageIds>({
           fix(fixer) {
             return fixer.removeRange([
               punctuatorTokenEnd.range[1],
-              nextNode.range[0],
+              typeAnnotation.range[0],
             ])
           },
         })
       }
 
-      if (before && previousDelta === 0) {
+      const hasPrevSpace = sourceCode.isSpaceBetween(previousToken, punctuatorTokenStart)
+
+      if (before && !hasPrevSpace) {
         context.report({
           node: punctuatorTokenStart,
           messageId: 'expectedSpaceBefore',
@@ -253,7 +254,7 @@ export default createRule<Options, MessageIds>({
           },
         })
       }
-      else if (!before && previousDelta > 0) {
+      else if (!before && hasPrevSpace) {
         context.report({
           node: punctuatorTokenStart,
           messageId: 'unexpectedSpaceBefore',