diff --git a/spacy/matcher/dependencymatcher.pyx b/spacy/matcher/dependencymatcher.pyx
index 0cda37012..b667e6b2f 100644
--- a/spacy/matcher/dependencymatcher.pyx
+++ b/spacy/matcher/dependencymatcher.pyx
@@ -177,13 +177,14 @@ cdef class DependencyMatcher:
 
         # Add 'RIGHT_ATTRS' to self._patterns[key]
         _patterns = [[[pat["RIGHT_ATTRS"]] for pat in pattern] for pattern in patterns]
+        pattern_offset = len(self._patterns[key])
         self._patterns[key].extend(_patterns)
 
         # Add each node pattern of all the input patterns individually to the
         # matcher. This enables only a single instance of Matcher to be used.
         # Multiple adds are required to track each node pattern.
         tokens_to_key_list = []
-        for i, current_patterns in enumerate(_patterns):
+        for i, current_patterns in enumerate(_patterns, start=pattern_offset):
 
             # Preallocate list space
             tokens_to_key = [None] * len(current_patterns)
@@ -263,7 +264,9 @@ cdef class DependencyMatcher:
         self._raw_patterns.pop(key)
         self._tree.pop(key)
         self._root.pop(key)
-        self._tokens_to_key.pop(key)
+        for mklist in self._tokens_to_key.pop(key):
+            for mkey in mklist:
+                self._matcher.remove(mkey)
 
     def _get_keys_to_position_maps(self, doc):
         """
diff --git a/spacy/tests/matcher/test_dependency_matcher.py b/spacy/tests/matcher/test_dependency_matcher.py
index 0e1eae588..61ae43c52 100644
--- a/spacy/tests/matcher/test_dependency_matcher.py
+++ b/spacy/tests/matcher/test_dependency_matcher.py
@@ -368,3 +368,87 @@ def test_dependency_matcher_span_user_data(en_tokenizer):
         assert doc_match[0] == span_match[0]
         for doc_t_i, span_t_i in zip(doc_match[1], span_match[1]):
             assert doc_t_i == span_t_i + offset
+
+
+def test_dependency_matcher_order_issue(en_tokenizer):
+    # issue from #9263
+    doc = en_tokenizer("I like text")
+    doc[2].head = doc[1]
+
+    # this matches on attrs but not rel op
+    pattern1 = [
+        {"RIGHT_ID": "root", "RIGHT_ATTRS": {"ORTH": "like"}},
+        {
+            "LEFT_ID": "root",
+            "RIGHT_ID": "r",
+            "RIGHT_ATTRS": {"ORTH": "text"},
+            "REL_OP": "<",
+        },
+    ]
+
+    # this matches on rel op but not attrs
+    pattern2 = [
+        {"RIGHT_ID": "root", "RIGHT_ATTRS": {"ORTH": "like"}},
+        {
+            "LEFT_ID": "root",
+            "RIGHT_ID": "r",
+            "RIGHT_ATTRS": {"ORTH": "fish"},
+            "REL_OP": ">",
+        },
+    ]
+
+    matcher = DependencyMatcher(en_tokenizer.vocab)
+
+    # This should behave the same as the next pattern
+    matcher.add("check", [pattern1, pattern2])
+    matches = matcher(doc)
+
+    assert matches == []
+
+    # use a new matcher
+    matcher = DependencyMatcher(en_tokenizer.vocab)
+    # adding one at a time under same label gets a match
+    matcher.add("check", [pattern1])
+    matcher.add("check", [pattern2])
+    matches = matcher(doc)
+
+    assert matches == []
+
+
+def test_dependency_matcher_remove(en_tokenizer):
+    # issue from #9263
+    doc = en_tokenizer("The red book")
+    doc[1].head = doc[2]
+
+    # this matches
+    pattern1 = [
+        {"RIGHT_ID": "root", "RIGHT_ATTRS": {"ORTH": "book"}},
+        {
+            "LEFT_ID": "root",
+            "RIGHT_ID": "r",
+            "RIGHT_ATTRS": {"ORTH": "red"},
+            "REL_OP": ">",
+        },
+    ]
+
+    # add and then remove it
+    matcher = DependencyMatcher(en_tokenizer.vocab)
+    matcher.add("check", [pattern1])
+    matcher.remove("check")
+
+    # this matches on rel op but not attrs
+    pattern2 = [
+        {"RIGHT_ID": "root", "RIGHT_ATTRS": {"ORTH": "flag"}},
+        {
+            "LEFT_ID": "root",
+            "RIGHT_ID": "r",
+            "RIGHT_ATTRS": {"ORTH": "blue"},
+            "REL_OP": ">",
+        },
+    ]
+
+    # Adding this new pattern with the same label, which should not match
+    matcher.add("check", [pattern2])
+    matches = matcher(doc)
+
+    assert matches == []