diff --git a/CHANGELOG.md b/CHANGELOG.md
index 622318f7..afd6f709 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -19,6 +19,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 from online detectors & interactors) (<https://github.com/opencv/cvat/pull/4543>)
 - Added Webhooks (<https://github.com/opencv/cvat/pull/4863>)
 - Authentication with social accounts google & github (<https://github.com/opencv/cvat/pull/5147>)
+- REST API tests to export job datasets & annotations and validate their structure  (<https://github.com/opencv/cvat/pull/5160>)
 
 ### Changed
 - `api/docs`, `api/swagger`, `api/schema`, `server/about` endpoints now allow unauthorized access (<https://github.com/opencv/cvat/pull/4928>, <https://github.com/opencv/cvat/pull/4935>)
diff --git a/cvat/apps/dataset_manager/task.py b/cvat/apps/dataset_manager/task.py
index d1d6af67..fdedb494 100644
--- a/cvat/apps/dataset_manager/task.py
+++ b/cvat/apps/dataset_manager/task.py
@@ -70,9 +70,18 @@ def _merge_table_rows(rows, keys_for_merge, field_id):
     return list(merged_rows.values())
 
 class JobAnnotation:
-    def __init__(self, pk):
-        self.db_job = models.Job.objects.select_related('segment__task') \
-            .select_for_update().get(id=pk)
+    def __init__(self, pk, is_prefetched=False):
+        if is_prefetched:
+            self.db_job = models.Job.objects.select_related('segment__task') \
+                .select_for_update().get(id=pk)
+        else:
+            self.db_job = models.Job.objects.prefetch_related(
+                'segment',
+                'segment__task',
+                Prefetch('segment__task__data', queryset=models.Data.objects.select_related('video').prefetch_related(
+                    Prefetch('images', queryset=models.Image.objects.order_by('frame'))
+                ))
+            ).get(pk=pk)
 
         db_segment = self.db_job.segment
         self.start_frame = db_segment.start_frame
@@ -630,7 +639,7 @@ class TaskAnnotation:
         self.reset()
 
         for db_job in self.db_jobs:
-            annotation = JobAnnotation(db_job.id)
+            annotation = JobAnnotation(db_job.id, is_prefetched=True)
             annotation.init_from_db()
             if annotation.ir_data.version > self.ir_data.version:
                 self.ir_data.version = annotation.ir_data.version
diff --git a/tests/python/README.md b/tests/python/README.md
index 3cc30e17..eff40c5e 100644
--- a/tests/python/README.md
+++ b/tests/python/README.md
@@ -68,8 +68,8 @@ for i, color in enumerate(colormap):
 To backup DB and data volume, please use commands below.
 
 ```console
-docker exec test_cvat_server_1 python manage.py dumpdata --indent 2 --natural-foreign --exclude=auth.permission --exclude=contenttypes > assets/cvat_db/data.json
-docker exec test_cvat_server_1 tar -cjv /home/django/data > assets/cvat_db/cvat_data.tar.bz2
+docker exec test_cvat_server_1 python manage.py dumpdata --indent 2 --natural-foreign --exclude=auth.permission --exclude=contenttypes > shared/assets/cvat_db/data.json
+docker exec test_cvat_server_1 tar -cjv /home/django/data > shared/assets/cvat_db/cvat_data.tar.bz2
 ```
 
 > Note: if you won't be use --indent options or will be use with other value
@@ -166,7 +166,7 @@ Assets directory has two parts:
    ```
    Just dump JSON assets with:
    ```
-   python3 tests/python/shared/utils/dump_objests.py
+   python3 tests/python/shared/utils/dump_objects.py
    ```
 
 1. If your test infrastructure has been corrupted and you have errors during db restoring.
diff --git a/tests/python/rest_api/test_jobs.py b/tests/python/rest_api/test_jobs.py
index 2cd03b02..ee6b9f5a 100644
--- a/tests/python/rest_api/test_jobs.py
+++ b/tests/python/rest_api/test_jobs.py
@@ -4,8 +4,11 @@
 # SPDX-License-Identifier: MIT
 
 import json
+import xml.etree.ElementTree as ET
+import zipfile
 from copy import deepcopy
 from http import HTTPStatus
+from io import BytesIO
 from typing import List
 
 import pytest
@@ -489,6 +492,36 @@ class TestPatchJob:
                 assert response.status == HTTPStatus.FORBIDDEN
 
 
+def _check_coco_job_annotations(content, values_to_be_checked):
+    exported_annotations = json.loads(content)
+    assert values_to_be_checked["shapes_length"] == len(exported_annotations["annotations"])
+    assert values_to_be_checked["job_size"] == len(exported_annotations["images"])
+    assert values_to_be_checked["task_size"] > len(exported_annotations["images"])
+
+
+def _check_cvat_job_annotations(content, values_to_be_checked):
+    document = ET.fromstring(content)
+    # check meta information
+    meta = document.find("meta")
+    instance = list(meta)[0]
+    assert instance.tag == "job"
+    assert instance.find("id").text == values_to_be_checked["job_id"]
+    assert instance.find("size").text == str(values_to_be_checked["job_size"])
+    assert instance.find("start_frame").text == str(values_to_be_checked["start_frame"])
+    assert instance.find("stop_frame").text == str(values_to_be_checked["stop_frame"])
+    assert instance.find("mode").text == values_to_be_checked["mode"]
+    assert len(instance.find("segments")) == 1
+
+    # check number of images, their sorting, number of annotations
+    images = document.findall("image")
+    assert len(images) == values_to_be_checked["job_size"]
+    assert len(list(document.iter("box"))) == values_to_be_checked["shapes_length"]
+    current_id = values_to_be_checked["start_frame"]
+    for image_elem in images:
+        assert image_elem.attrib["id"] == str(current_id)
+        current_id += 1
+
+
 @pytest.mark.usefixtures("restore_db_per_class")
 class TestJobDataset:
     def _export_dataset(self, username, jid, **kwargs):
@@ -510,3 +543,45 @@ class TestJobDataset:
         job = jobs_with_shapes[0]
         response = self._export_annotations(admin_user, job["id"], format="CVAT for images 1.1")
         assert response.data
+
+    @pytest.mark.parametrize("username, jid", [("admin1", 14)])
+    @pytest.mark.parametrize(
+        "anno_format, anno_file_name, check_func",
+        [
+            ("COCO 1.0", "annotations/instances_default.json", _check_coco_job_annotations),
+            ("CVAT for images 1.1", "annotations.xml", _check_cvat_job_annotations),
+        ],
+    )
+    def test_exported_job_dataset_structure(
+        self,
+        username,
+        jid,
+        anno_format,
+        anno_file_name,
+        check_func,
+        tasks,
+        jobs,
+        annotations,
+    ):
+        job_data = jobs[jid]
+        annotations_before = annotations["job"][str(jid)]
+
+        values_to_be_checked = {
+            "task_size": tasks[job_data["task_id"]]["size"],
+            # NOTE: data step is not stored in assets, default = 1
+            "job_size": job_data["stop_frame"] - job_data["start_frame"] + 1,
+            "start_frame": job_data["start_frame"],
+            "stop_frame": job_data["stop_frame"],
+            "shapes_length": len(annotations_before["shapes"]),
+            "job_id": str(jid),
+            "mode": job_data["mode"],
+        }
+
+        response = self._export_dataset(username, jid, format=anno_format)
+        assert response.data
+        with zipfile.ZipFile(BytesIO(response.data)) as zip_file:
+            assert (
+                len(zip_file.namelist()) == values_to_be_checked["job_size"] + 1
+            )  # images + annotation file
+            content = zip_file.read(anno_file_name)
+        check_func(content, values_to_be_checked)
diff --git a/tests/python/shared/assets/annotations.json b/tests/python/shared/assets/annotations.json
index c93ee597..80fe0133 100644
--- a/tests/python/shared/assets/annotations.json
+++ b/tests/python/shared/assets/annotations.json
@@ -280,7 +280,53 @@
       "version": 0
     },
     "14": {
-      "shapes": [],
+      "shapes": [
+        {
+          "attributes": [],
+          "elements": [],
+          "frame": 15,
+          "group": 0,
+          "id": 41,
+          "label_id": 6,
+          "occluded": false,
+          "outside": false,
+          "points": [
+            53.062929061787145,
+            301.6390160183091,
+            197.94851258581548,
+            763.3266590389048
+          ],
+          "rotation": 0.0,
+          "source": "manual",
+          "type": "rectangle",
+          "z_order": 0
+        },
+        {
+          "attributes": [
+            {
+              "spec_id": 1,
+              "value": "mazda"
+            }
+          ],
+          "elements": [],
+          "frame": 16,
+          "group": 0,
+          "id": 42,
+          "label_id": 5,
+          "occluded": false,
+          "outside": false,
+          "points": [
+            172.0810546875,
+            105.990234375,
+            285.97262095255974,
+            138.40000000000146
+          ],
+          "rotation": 0.0,
+          "source": "manual",
+          "type": "rectangle",
+          "z_order": 0
+        }
+      ],
       "tags": [],
       "tracks": [],
       "version": 0
@@ -932,6 +978,51 @@
           "source": "manual",
           "type": "rectangle",
           "z_order": 0
+        },
+        {
+          "attributes": [],
+          "elements": [],
+          "frame": 15,
+          "group": 0,
+          "id": 41,
+          "label_id": 6,
+          "occluded": false,
+          "outside": false,
+          "points": [
+            53.062929061787145,
+            301.6390160183091,
+            197.94851258581548,
+            763.3266590389048
+          ],
+          "rotation": 0.0,
+          "source": "manual",
+          "type": "rectangle",
+          "z_order": 0
+        },
+        {
+          "attributes": [
+            {
+              "spec_id": 1,
+              "value": "mazda"
+            }
+          ],
+          "elements": [],
+          "frame": 16,
+          "group": 0,
+          "id": 42,
+          "label_id": 5,
+          "occluded": false,
+          "outside": false,
+          "points": [
+            172.0810546875,
+            105.990234375,
+            285.97262095255974,
+            138.40000000000146
+          ],
+          "rotation": 0.0,
+          "source": "manual",
+          "type": "rectangle",
+          "z_order": 0
         }
       ],
       "tags": [],
diff --git a/tests/python/shared/assets/cvat_db/cvat_data.tar.bz2 b/tests/python/shared/assets/cvat_db/cvat_data.tar.bz2
index cec26a03..d05fa40c 100644
Binary files a/tests/python/shared/assets/cvat_db/cvat_data.tar.bz2 and b/tests/python/shared/assets/cvat_db/cvat_data.tar.bz2 differ
diff --git a/tests/python/shared/assets/cvat_db/data.json b/tests/python/shared/assets/cvat_db/data.json
index 1b4a382b..3c371804 100644
--- a/tests/python/shared/assets/cvat_db/data.json
+++ b/tests/python/shared/assets/cvat_db/data.json
@@ -36,7 +36,7 @@
   "pk": 1,
   "fields": {
     "password": "pbkdf2_sha256$260000$DevmxlmLwciP1P6sZs2Qag$U9DFtjTWx96Sk95qY6UXVcvpdQEP2LcoFBftk5D2RKY=",
-    "last_login": "2022-10-17T17:09:16.903Z",
+    "last_login": "2022-11-03T13:56:42.744Z",
     "is_superuser": true,
     "username": "admin1",
     "first_name": "Admin",
@@ -2192,7 +2192,7 @@
     ],
     "bug_tracker": "",
     "created_date": "2021-12-14T19:46:37.969Z",
-    "updated_date": "2022-03-05T09:47:49.679Z",
+    "updated_date": "2022-11-03T13:57:25.895Z",
     "status": "annotation",
     "organization": null,
     "source_storage": null,
@@ -2463,7 +2463,7 @@
     ],
     "bug_tracker": "",
     "created_date": "2022-03-05T09:33:10.420Z",
-    "updated_date": "2022-03-05T09:47:49.667Z",
+    "updated_date": "2022-11-03T13:57:26.007Z",
     "overlap": 0,
     "segment_size": 5,
     "status": "annotation",
@@ -3556,10 +3556,10 @@
   "fields": {
     "segment": 14,
     "assignee": null,
-    "updated_date": "2022-06-22T09:18:45.296Z",
+    "updated_date": "2022-11-03T13:57:26.346Z",
     "status": "annotation",
     "stage": "annotation",
-    "state": "new"
+    "state": "in progress"
   }
 },
 {
@@ -4751,6 +4751,55 @@
     "job": 17
   }
 },
+{
+  "model": "engine.jobcommit",
+  "pk": 74,
+  "fields": {
+    "scope": "create",
+    "owner": [
+      "business1"
+    ],
+    "timestamp": "2022-11-03T13:57:26.015Z",
+    "data": {
+      "stage": "annotation",
+      "state": "new",
+      "assignee": null
+    },
+    "job": 14
+  }
+},
+{
+  "model": "engine.jobcommit",
+  "pk": 75,
+  "fields": {
+    "scope": "create",
+    "owner": [
+      "business1"
+    ],
+    "timestamp": "2022-11-03T13:57:26.351Z",
+    "data": {
+      "stage": "annotation",
+      "state": "in progress",
+      "assignee": null
+    },
+    "job": 14
+  }
+},
+{
+  "model": "engine.jobcommit",
+  "pk": 76,
+  "fields": {
+    "scope": "update",
+    "owner": [
+      "admin1"
+    ],
+    "timestamp": "2022-11-03T13:57:26.356Z",
+    "data": {
+      "state": "in progress"
+    },
+    "job": 14
+  }
+},
 {
   "model": "engine.labeledimage",
   "pk": 1,
@@ -5079,6 +5128,42 @@
     "parent": 36
   }
 },
+{
+  "model": "engine.labeledshape",
+  "pk": 41,
+  "fields": {
+    "job": 14,
+    "label": 6,
+    "frame": 15,
+    "group": 0,
+    "source": "manual",
+    "type": "rectangle",
+    "occluded": false,
+    "outside": false,
+    "z_order": 0,
+    "points": "[53.062929061787145, 301.6390160183091, 197.94851258581548, 763.3266590389048]",
+    "rotation": 0.0,
+    "parent": null
+  }
+},
+{
+  "model": "engine.labeledshape",
+  "pk": 42,
+  "fields": {
+    "job": 14,
+    "label": 5,
+    "frame": 16,
+    "group": 0,
+    "source": "manual",
+    "type": "rectangle",
+    "occluded": false,
+    "outside": false,
+    "z_order": 0,
+    "points": "[172.0810546875, 105.990234375, 285.97262095255974, 138.40000000000146]",
+    "rotation": 0.0,
+    "parent": null
+  }
+},
 {
   "model": "engine.labeledshapeattributeval",
   "pk": 1,
@@ -5097,6 +5182,15 @@
     "shape": 39
   }
 },
+{
+  "model": "engine.labeledshapeattributeval",
+  "pk": 3,
+  "fields": {
+    "spec": 1,
+    "value": "mazda",
+    "shape": 42
+  }
+},
 {
   "model": "engine.labeledtrack",
   "pk": 1,
@@ -5920,6 +6014,85 @@
     "organization": 1
   }
 },
+{
+  "model": "webhooks.webhookdelivery",
+  "pk": 1,
+  "fields": {
+    "webhook": 2,
+    "event": "update:job",
+    "status_code": 200,
+    "redelivery": false,
+    "created_date": "2022-11-03T13:57:26.380Z",
+    "updated_date": "2022-11-03T13:57:26.908Z",
+    "changed_fields": "state",
+    "request": {
+      "job": {
+        "id": 14,
+        "url": "http://localhost:8080/api/jobs/14",
+        "mode": "annotation",
+        "stage": "annotation",
+        "state": "in progress",
+        "labels": [
+          {
+            "id": 6,
+            "name": "person",
+            "type": "any",
+            "color": "#c06060",
+            "sublabels": [],
+            "attributes": [],
+            "has_parent": false
+          },
+          {
+            "id": 5,
+            "name": "car",
+            "type": "any",
+            "color": "#2080c0",
+            "sublabels": [],
+            "attributes": [
+              {
+                "id": 1,
+                "name": "model",
+                "values": [
+                  "mazda",
+                  "volvo",
+                  "bmw"
+                ],
+                "mutable": false,
+                "input_type": "select",
+                "default_value": "mazda"
+              }
+            ],
+            "has_parent": false
+          }
+        ],
+        "status": "annotation",
+        "task_id": 9,
+        "assignee": null,
+        "dimension": "2d",
+        "project_id": 1,
+        "stop_frame": 19,
+        "bug_tracker": "",
+        "start_frame": 15,
+        "updated_date": "2022-11-03T13:57:26.346824Z",
+        "data_chunk_size": 72,
+        "data_compressed_chunk_type": "imageset"
+      },
+      "event": "update:job",
+      "sender": {
+        "id": 1,
+        "url": "http://localhost:8080/api/users/1",
+        "username": "admin1",
+        "last_name": "First",
+        "first_name": "Admin"
+      },
+      "webhook_id": 2,
+      "before_update": {
+        "state": "new"
+      }
+    },
+    "response": "<!doctype html>\n<html>\n<head>\n    <title>Example Domain</title>\n\n    <meta charset=\"utf-8\" />\n    <meta http-equiv=\"Content-type\" content=\"text/html; charset=utf-8\" />\n    <meta name=\"viewport\" content=\"width=device-width, initial-scale=1\" />\n    <style type=\"text/css\">\n    body {\n        background-color: #f0f0f2;\n        margin: 0;\n        padding: 0;\n        font-family: -apple-system, system-ui, BlinkMacSystemFont, \"Segoe UI\", \"Open Sans\", \"Helvetica Neue\", Helvetica, Arial, sans-serif;\n        \n    }\n    div {\n        width: 600px;\n        margin: 5em auto;\n        padding: 2em;\n        background-color: #fdfdff;\n        border-radius: 0.5em;\n        box-shadow: 2px 3px 7px 2px rgba(0,0,0,0.02);\n    }\n    a:link, a:visited {\n        color: #38488f;\n        text-decoration: none;\n    }\n    @media (max-width: 700px) {\n        div {\n            margin: 0 auto;\n            width: auto;\n        }\n    }\n    </style>    \n</head>\n\n<body>\n<div>\n    <h1>Example Domain</h1>\n    <p>This domain is for use in illustrative examples in documents. You may use this\n    domain in literature without prior coordination or asking for permission.</p>\n    <p><a href=\"https://www.iana.org/domains/example\">More information...</a></p>\n</div>\n</body>\n</html>\n"
+  }
+},
 {
   "model": "admin.logentry",
   "pk": 1,
diff --git a/tests/python/shared/assets/jobs.json b/tests/python/shared/assets/jobs.json
index c1c10d25..2c65db5f 100644
--- a/tests/python/shared/assets/jobs.json
+++ b/tests/python/shared/assets/jobs.json
@@ -326,11 +326,11 @@
       "project_id": 1,
       "stage": "annotation",
       "start_frame": 15,
-      "state": "new",
+      "state": "in progress",
       "status": "annotation",
       "stop_frame": 19,
       "task_id": 9,
-      "updated_date": "2022-06-22T09:18:45.296000Z",
+      "updated_date": "2022-11-03T13:57:26.346000Z",
       "url": "http://localhost:8080/api/jobs/14"
     },
     {
diff --git a/tests/python/shared/assets/projects.json b/tests/python/shared/assets/projects.json
index 8dd2a11e..51e9ee02 100644
--- a/tests/python/shared/assets/projects.json
+++ b/tests/python/shared/assets/projects.json
@@ -508,7 +508,7 @@
       "tasks": [
         9
       ],
-      "updated_date": "2022-03-05T09:47:49.679000Z",
+      "updated_date": "2022-11-03T13:57:25.895000Z",
       "url": "http://localhost:8080/api/projects/1"
     }
   ]
diff --git a/tests/python/shared/assets/tasks.json b/tests/python/shared/assets/tasks.json
index 91308d46..9642092f 100644
--- a/tests/python/shared/assets/tasks.json
+++ b/tests/python/shared/assets/tasks.json
@@ -550,7 +550,7 @@
               "assignee": null,
               "id": 14,
               "stage": "annotation",
-              "state": "new",
+              "state": "in progress",
               "status": "annotation",
               "url": "http://localhost:8080/api/jobs/14"
             }
@@ -564,7 +564,7 @@
       "status": "annotation",
       "subset": "",
       "target_storage": null,
-      "updated_date": "2022-03-05T09:47:49.667000Z",
+      "updated_date": "2022-11-03T13:57:26.007000Z",
       "url": "http://localhost:8080/api/tasks/9"
     },
     {
diff --git a/tests/python/shared/assets/users.json b/tests/python/shared/assets/users.json
index 4fe99c39..83e6ad10 100644
--- a/tests/python/shared/assets/users.json
+++ b/tests/python/shared/assets/users.json
@@ -310,7 +310,7 @@
       "is_active": true,
       "is_staff": true,
       "is_superuser": true,
-      "last_login": "2022-10-17T17:09:16.903140Z",
+      "last_login": "2022-11-03T13:56:42.744000Z",
       "last_name": "First",
       "url": "http://localhost:8080/api/users/1",
       "username": "admin1"
diff --git a/tests/python/shared/assets/webhooks.json b/tests/python/shared/assets/webhooks.json
index ec2a71bd..f2cbe54c 100644
--- a/tests/python/shared/assets/webhooks.json
+++ b/tests/python/shared/assets/webhooks.json
@@ -91,6 +91,8 @@
       ],
       "id": 2,
       "is_active": true,
+      "last_delivery_date": "2022-11-03T13:57:26.908000Z",
+      "last_status": 200,
       "organization": null,
       "owner": {
         "first_name": "Business",