diff --git a/sdk/core/azure-core/CHANGELOG.md b/sdk/core/azure-core/CHANGELOG.md
index 213564f6755c..ec1e97608c35 100644
--- a/sdk/core/azure-core/CHANGELOG.md
+++ b/sdk/core/azure-core/CHANGELOG.md
@@ -6,6 +6,8 @@
 
 ### Breaking Changes
 
+- Sync stream downloading now raises `azure.core.exceptions.DecodeError` rather than `requests.exceptions.ContentDecodingError`
+
 ### Bugs Fixed
 
 ### Other Changes
diff --git a/sdk/core/azure-core/azure/core/pipeline/transport/_requests_basic.py b/sdk/core/azure-core/azure/core/pipeline/transport/_requests_basic.py
index ab9807e7bdc0..3896ad825d02 100644
--- a/sdk/core/azure-core/azure/core/pipeline/transport/_requests_basic.py
+++ b/sdk/core/azure-core/azure/core/pipeline/transport/_requests_basic.py
@@ -29,7 +29,7 @@
 import urllib3 # type: ignore
 from urllib3.util.retry import Retry # type: ignore
 from urllib3.exceptions import (
-    DecodeError, ReadTimeoutError, ProtocolError
+    DecodeError as CoreDecodeError, ReadTimeoutError, ProtocolError
 )
 import requests
 
@@ -39,6 +39,7 @@
     ServiceResponseError,
     IncompleteReadError,
     HttpResponseError,
+    DecodeError
 )
 from . import HttpRequest # pylint: disable=unused-import
 
@@ -71,11 +72,11 @@ def _read_raw_stream(response, chunk_size=1):
             for chunk in response.raw.stream(chunk_size, decode_content=False):
                 yield chunk
         except ProtocolError as e:
-            raise requests.exceptions.ChunkedEncodingError(e)
-        except DecodeError as e:
-            raise requests.exceptions.ContentDecodingError(e)
+            raise ServiceResponseError(e, error=e)
+        except CoreDecodeError as e:
+            raise DecodeError(e, error=e)
         except ReadTimeoutError as e:
-            raise requests.exceptions.ConnectionError(e)
+            raise ServiceRequestError(e, error=e)
     else:
         # Standard file-like object.
         while True:
@@ -174,6 +175,8 @@ def __next__(self):
             raise StopIteration()
         except requests.exceptions.StreamConsumedError:
             raise
+        except requests.exceptions.ContentDecodingError as err:
+            raise DecodeError(err, error=err)
         except requests.exceptions.ChunkedEncodingError as err:
             msg = err.__str__()
             if 'IncompleteRead' in msg:
diff --git a/sdk/core/azure-core/tests/test_streaming.py b/sdk/core/azure-core/tests/test_streaming.py
index 87e51851722f..17f9d82f612e 100644
--- a/sdk/core/azure-core/tests/test_streaming.py
+++ b/sdk/core/azure-core/tests/test_streaming.py
@@ -97,7 +97,6 @@ def test_compress_compressed_no_header(http_request):
 @pytest.mark.parametrize("http_request", HTTP_REQUESTS)
 def test_decompress_plain_header(http_request):
     # expect error
-    import requests
     account_name = "coretests"
     account_url = "https://{}.blob.core.windows.net".format(account_name)
     url = "https://{}.blob.core.windows.net/tests/test_with_header.txt".format(account_name)
@@ -109,7 +108,7 @@ def test_decompress_plain_header(http_request):
     try:
         content = b"".join(list(data))
         assert False
-    except (requests.exceptions.ContentDecodingError, DecodeError):
+    except DecodeError:
         pass
 
 @pytest.mark.parametrize("http_request", HTTP_REQUESTS)