diff --git a/googleapiclient/http.py b/googleapiclient/http.py
index 926ca1b..a875751 100644
--- a/googleapiclient/http.py
+++ b/googleapiclient/http.py
@@ -1026,13 +1026,17 @@
             chunk_end = self.resumable_progress + len(data) - 1
 
         headers = {
-            "Content-Range": "bytes %d-%d/%s"
-            % (self.resumable_progress, chunk_end, size),
             # Must set the content-length header here because httplib can't
             # calculate the size when working with _StreamSlice.
             "Content-Length": str(chunk_end - self.resumable_progress + 1),
         }
 
+        # An empty file results in chunk_end = -1 and size = 0
+        # sending "bytes 0--1/0" results in an invalid request
+        # Only add header "Content-Range" if chunk_end != -1
+        if chunk_end != -1:
+            headers["Content-Range"] = "bytes %d-%d/%s" % (self.resumable_progress, chunk_end, size)
+
         for retry_num in range(num_retries + 1):
             if retry_num > 0:
                 self._sleep(self._rand() * 2 ** retry_num)
diff --git a/tests/test_http.py b/tests/test_http.py
index 2d74a7e..c7d9cc3 100644
--- a/tests/test_http.py
+++ b/tests/test_http.py
@@ -443,6 +443,33 @@
         request._sleep.assert_not_called()
 
 
+    def test_media_io_base_empty_file(self):
+        fd = BytesIO()
+        upload = MediaIoBaseUpload(
+            fd=fd, mimetype="image/png", chunksize=500, resumable=True
+        )
+
+        http = HttpMockSequence(
+            [
+                ({"status": "200", "location": "https://www.googleapis.com/someapi/v1/upload?foo=bar"}, "{}"),
+                ({"status": "200", "location": "https://www.googleapis.com/someapi/v1/upload?foo=bar"}, "{}")
+            ]
+        )
+
+        model = JsonModel()
+        uri = u"https://www.googleapis.com/someapi/v1/upload/?foo=bar"
+        method = u"POST"
+        request = HttpRequest(
+            http, model.response, uri, method=method, headers={}, resumable=upload
+        )
+
+        request.execute()
+
+        # Check that "Content-Range" header is not set in the PUT request
+        self.assertTrue("Content-Range" not in http.request_sequence[-1][-1])
+        self.assertEqual("0", http.request_sequence[-1][-1]["Content-Length"])
+
+
 class TestMediaIoBaseDownload(unittest.TestCase):
     def setUp(self):
         http = HttpMock(datafile("zoo.json"), {"status": "200"})