diff --git a/docs/webhook-config.md b/docs/webhook-config.md
index ec944cb50..bea555385 100644
--- a/docs/webhook-config.md
+++ b/docs/webhook-config.md
@@ -50,7 +50,7 @@ Sample configuration (tested using IFTTT).
 
 The url in `webhook.url` should point to the correct url for your webhook. If you're using [IFTTT](https://ifttt.com) (as shown in the sample above) please insert your event and key to the url.
 
-You can set the POST body format to Form-Encoded (default) or JSON-Encoded. Use `"format": "form"` or `"format": "json"` respectively. Example configuration for Mattermost Cloud integration:
+You can set the POST body format to Form-Encoded (default), JSON-Encoded, or raw data. Use `"format": "form"`, `"format": "json"`, or `"format": "raw"` respectively. Example configuration for Mattermost Cloud integration:
 
 ```json
   "webhook": {
@@ -63,7 +63,36 @@ You can set the POST body format to Form-Encoded (default) or JSON-Encoded. Use
     },
 ```
 
-The result would be POST request with e.g. `{"text":"Status: running"}` body and `Content-Type: application/json` header which results `Status: running` message in the Mattermost channel.
+The result would be a POST request with e.g. `{"text":"Status: running"}` body and `Content-Type: application/json` header which results `Status: running` message in the Mattermost channel.
+
+When using the Form-Encoded or JSON-Encoded configuration you can configure any number of payload values, and both the key and value will be ouput in the POST request. However, when using the raw data format you can only configure one value and it **must** be named `"data"`. In this instance the data key will not be output in the POST request, only the value. For example:
+
+```json
+  "webhook": {
+        "enabled": true,
+        "url": "https://<YOURHOOKURL>",
+        "format": "raw",
+        "webhookstatus": {
+            "data": "Status: {status}"
+        }
+    },
+```
+
+The result would be a POST request with e.g. `Status: running` body and `Content-Type: text/plain` header.
+
+Optional parameters are available to enable automatic retries for webhook messages. The `webhook.retries` parameter can be set for the maximum number of retries the webhook request should attempt if it is unsuccessful (i.e. HTTP response status is not 200). By default this is set to `0` which is disabled. An additional `webhook.retry_delay` parameter can be set to specify the time in seconds between retry attempts. By default this is set to `0.1` (i.e. 100ms). Note that increasing the number of retries or retry delay may slow down the trader if there are connectivity issues with the webhook. Example configuration for retries:
+
+```json
+  "webhook": {
+        "enabled": true,
+        "url": "https://<YOURHOOKURL>",
+        "retries": 3,
+        "retry_delay": 0.2,
+        "webhookstatus": {
+            "status": "Status: {status}"
+        }
+    },
+```
 
 Different payloads can be configured for different events. Not all fields are necessary, but you should configure at least one of the dicts, otherwise the webhook will never be called.
 
diff --git a/freqtrade/constants.py b/freqtrade/constants.py
index e775e39fc..e074718ca 100644
--- a/freqtrade/constants.py
+++ b/freqtrade/constants.py
@@ -50,6 +50,8 @@ USERPATH_STRATEGIES = 'strategies'
 USERPATH_NOTEBOOKS = 'notebooks'
 
 TELEGRAM_SETTING_OPTIONS = ['on', 'off', 'silent']
+WEBHOOK_FORMAT_OPTIONS = ['form', 'json', 'raw']
+
 ENV_VAR_PREFIX = 'FREQTRADE__'
 
 NON_OPEN_EXCHANGE_STATES = ('cancelled', 'canceled', 'closed', 'expired')
@@ -312,10 +314,16 @@ CONF_SCHEMA = {
             'type': 'object',
             'properties': {
                 'enabled': {'type': 'boolean'},
+                'url': {'type': 'string'},
+                'format': {'type': 'string', 'enum': WEBHOOK_FORMAT_OPTIONS, 'default': 'form'},
+                'retries': {'type': 'integer', 'minimum': 0},
+                'retry_delay': {'type': 'number', 'minimum': 0},
                 'webhookbuy': {'type': 'object'},
                 'webhookbuycancel': {'type': 'object'},
+                'webhookbuyfill': {'type': 'object'},
                 'webhooksell': {'type': 'object'},
                 'webhooksellcancel': {'type': 'object'},
+                'webhooksellfill': {'type': 'object'},
                 'webhookstatus': {'type': 'object'},
             },
         },
diff --git a/freqtrade/rpc/webhook.py b/freqtrade/rpc/webhook.py
index b4c55649e..58b75769e 100644
--- a/freqtrade/rpc/webhook.py
+++ b/freqtrade/rpc/webhook.py
@@ -2,6 +2,7 @@
 This module manages webhook communication
 """
 import logging
+import time
 from typing import Any, Dict
 
 from requests import RequestException, post
@@ -28,12 +29,9 @@ class Webhook(RPCHandler):
         super().__init__(rpc, config)
 
         self._url = self._config['webhook']['url']
-
         self._format = self._config['webhook'].get('format', 'form')
-
-        if self._format != 'form' and self._format != 'json':
-            raise NotImplementedError('Unknown webhook format `{}`, possible values are '
-                                      '`form` (default) and `json`'.format(self._format))
+        self._retries = self._config['webhook'].get('retries', 0)
+        self._retry_delay = self._config['webhook'].get('retry_delay', 0.1)
 
     def cleanup(self) -> None:
         """
@@ -77,13 +75,30 @@ class Webhook(RPCHandler):
     def _send_msg(self, payload: dict) -> None:
         """do the actual call to the webhook"""
 
-        try:
-            if self._format == 'form':
-                post(self._url, data=payload)
-            elif self._format == 'json':
-                post(self._url, json=payload)
-            else:
-                raise NotImplementedError('Unknown format: {}'.format(self._format))
+        success = False
+        attempts = 0
+        while not success and attempts <= self._retries:
+            if attempts:
+                if self._retry_delay:
+                    time.sleep(self._retry_delay)
+                logger.info("Retrying webhook...")
 
-        except RequestException as exc:
-            logger.warning("Could not call webhook url. Exception: %s", exc)
+            attempts += 1
+
+            try:
+                if self._format == 'form':
+                    response = post(self._url, data=payload)
+                elif self._format == 'json':
+                    response = post(self._url, json=payload)
+                elif self._format == 'raw':
+                    response = post(self._url, data=payload['data'],
+                                    headers={'Content-Type': 'text/plain'})
+                else:
+                    raise NotImplementedError('Unknown format: {}'.format(self._format))
+
+                # Throw a RequestException if the post was not successful
+                response.raise_for_status()
+                success = True
+
+            except RequestException as exc:
+                logger.warning("Could not call webhook url. Exception: %s", exc)
diff --git a/tests/rpc/test_rpc_webhook.py b/tests/rpc/test_rpc_webhook.py
index 04e63a3be..17d1baca9 100644
--- a/tests/rpc/test_rpc_webhook.py
+++ b/tests/rpc/test_rpc_webhook.py
@@ -292,3 +292,15 @@ def test__send_msg_with_json_format(default_conf, mocker, caplog):
     webhook._send_msg(msg)
 
     assert post.call_args[1] == {'json': msg}
+
+
+def test__send_msg_with_raw_format(default_conf, mocker, caplog):
+    default_conf["webhook"] = get_webhook_dict()
+    default_conf["webhook"]["format"] = "raw"
+    webhook = Webhook(RPC(get_patched_freqtradebot(mocker, default_conf)), default_conf)
+    msg = {'data': 'Hello'}
+    post = MagicMock()
+    mocker.patch("freqtrade.rpc.webhook.post", post)
+    webhook._send_msg(msg)
+
+    assert post.call_args[1] == {'data': msg['data'], 'headers': {'Content-Type': 'text/plain'}}