diff --git a/yt_dlp/extractor/vimeo.py b/yt_dlp/extractor/vimeo.py
index 18eb084449..d10689cd80 100644
--- a/yt_dlp/extractor/vimeo.py
+++ b/yt_dlp/extractor/vimeo.py
@@ -212,16 +212,6 @@ def _parse_config(self, config, video_id):
         owner = video_data.get('owner') or {}
         video_uploader_url = owner.get('url')
 
-        duration = int_or_none(video_data.get('duration'))
-        chapter_data = try_get(config, lambda x: x['embed']['chapters']) or []
-        chapters = [{
-            'title': current_chapter.get('title'),
-            'start_time': current_chapter.get('timecode'),
-            'end_time': next_chapter.get('timecode'),
-        } for current_chapter, next_chapter in zip(chapter_data, chapter_data[1:] + [{'timecode': duration}])]
-        if chapters and chapters[0]['start_time']:  # Chapters may not start from 0
-            chapters[:0] = [{'title': '<Untitled>', 'start_time': 0, 'end_time': chapters[0]['start_time']}]
-
         return {
             'id': str_or_none(video_data.get('id')) or video_id,
             'title': video_title,
@@ -229,8 +219,12 @@ def _parse_config(self, config, video_id):
             'uploader_id': video_uploader_url.split('/')[-1] if video_uploader_url else None,
             'uploader_url': video_uploader_url,
             'thumbnails': thumbnails,
-            'duration': duration,
-            'chapters': chapters or None,
+            'duration': int_or_none(video_data.get('duration')),
+            'chapters': sorted(traverse_obj(config, (
+                'embed', 'chapters', lambda _, v: int(v['timecode']) is not None, {
+                    'title': ('title', {str}),
+                    'start_time': ('timecode', {int_or_none}),
+                })), key=lambda c: c['start_time']) or None,
             'formats': formats,
             'subtitles': subtitles,
             'live_status': live_status,
@@ -708,6 +702,39 @@ class VimeoIE(VimeoBaseInfoExtractor):
                 'skip_download': True,
             },
         },
+        {
+            # chapters must be sorted, see: https://github.com/yt-dlp/yt-dlp/issues/5308
+            'url': 'https://player.vimeo.com/video/756714419',
+            'info_dict': {
+                'id': '756714419',
+                'ext': 'mp4',
+                'title': 'Dr Arielle Schwartz - Therapeutic yoga for optimum sleep',
+                'uploader': 'Alex Howard',
+                'uploader_id': 'user54729178',
+                'uploader_url': 'https://vimeo.com/user54729178',
+                'thumbnail': r're:https://i\.vimeocdn\.com/video/1520099929-[\da-f]+-d_1280',
+                'duration': 2636,
+                'chapters': [
+                    {'start_time': 0, 'end_time': 10, 'title': '<Untitled Chapter 1>'},
+                    {'start_time': 10, 'end_time': 106, 'title': 'Welcoming Dr Arielle Schwartz'},
+                    {'start_time': 106, 'end_time': 305, 'title': 'What is therapeutic yoga?'},
+                    {'start_time': 305, 'end_time': 594, 'title': 'Vagal toning practices'},
+                    {'start_time': 594, 'end_time': 888, 'title': 'Trauma and difficulty letting go'},
+                    {'start_time': 888, 'end_time': 1059, 'title': "Dr Schwartz' insomnia experience"},
+                    {'start_time': 1059, 'end_time': 1471, 'title': 'A strategy for helping sleep issues'},
+                    {'start_time': 1471, 'end_time': 1667, 'title': 'Yoga nidra'},
+                    {'start_time': 1667, 'end_time': 2121, 'title': 'Wisdom in stillness'},
+                    {'start_time': 2121, 'end_time': 2386, 'title': 'What helps us be more able to let go?'},
+                    {'start_time': 2386, 'end_time': 2510, 'title': 'Practical tips to help ourselves'},
+                    {'start_time': 2510, 'end_time': 2636, 'title': 'Where to find out more'},
+                ],
+            },
+            'params': {
+                'http_headers': {'Referer': 'https://sleepsuperconference.com'},
+                'skip_download': 'm3u8',
+            },
+            'expected_warnings': ['Failed to parse XML: not well-formed'],
+        },
         {
             # user playlist alias -> https://vimeo.com/258705797
             'url': 'https://vimeo.com/user26785108/newspiritualguide',