diff --git a/CHANGELOG b/CHANGELOG
index 44d5938e..cf5d4bc9 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -1,7 +1,7 @@
 Development Version
 -------------------
 
-Nothing yet.
+* Recognize CROSS APPLY and OUTER APPLY as keywords (issue300).
 
 
 Release 0.6.0 (Aug 13, 2026)
diff --git a/sqlparse/keywords.py b/sqlparse/keywords.py
index dd6e5d15..abd0ea5c 100644
--- a/sqlparse/keywords.py
+++ b/sqlparse/keywords.py
@@ -173,6 +173,7 @@ def find_delimited_spans(text):
     (r'(?<![\w\])])(\[[^\]\[]+\])', tokens.Name),
     (r'((LEFT\s+|RIGHT\s+|FULL\s+)?(INNER\s+|OUTER\s+|STRAIGHT\s+)?'
      r'|(CROSS\s+|NATURAL\s+)?)?JOIN\b', tokens.Keyword),
+    (r'(CROSS|OUTER)\s+APPLY(?![\w$#])', tokens.Keyword),
     (r'END(\s+IF|\s+LOOP|\s+WHILE|\s+FOR|\s+CASE)?\b', tokens.Keyword),
     (r'IF\s+(NOT\s+)?EXISTS\b', tokens.Keyword),
     (r'NOT\s+NULL\b', tokens.Keyword),
diff --git a/tests/test_apply.py b/tests/test_apply.py
new file mode 100644
index 00000000..f4a9d8d6
--- /dev/null
+++ b/tests/test_apply.py
@@ -0,0 +1,68 @@
+import pytest
+
+import sqlparse
+from sqlparse import lexer, sql
+from sqlparse import tokens as T
+
+APPLY_OPERATORS = [
+    'CROSS APPLY', 'OUTER APPLY', 'cross  apply', 'outer\tapply',
+    'CrOsS\nApPlY', 'OuTeR\r\nApPlY',
+]
+
+
+@pytest.mark.parametrize('operator', APPLY_OPERATORS)
+def test_apply_keyword(operator):
+    assert list(lexer.tokenize(operator)) == [(T.Keyword, operator)]
+
+
+@pytest.mark.parametrize('operator', ['CROSS APPLY', 'OUTER APPLY'])
+@pytest.mark.parametrize('right', [
+    'dbo.GetReports(d.DeptMgrID) r',
+    'OPENJSON(d.payload) r',
+    '(select d.DeptMgrID as id) r',
+])
+def test_apply_table_sources(operator, right):
+    query = f'select * from Departments d {operator} {right}'
+    statement = sqlparse.parse(query)[0]
+    tokens = [token for token in statement if not token.is_whitespace]
+
+    assert len(tokens) == 6
+    assert isinstance(tokens[3], sql.Identifier)
+    assert tokens[3].get_real_name() == 'Departments'
+    assert tokens[3].get_alias() == 'd'
+    assert tokens[4].match(T.Keyword, operator)
+    assert isinstance(tokens[5], sql.Identifier)
+    assert tokens[5].value == right
+    assert tokens[5].get_alias() == 'r'
+    assert str(statement) == query
+
+
+@pytest.mark.parametrize('operator', APPLY_OPERATORS)
+@pytest.mark.parametrize('case', ['upper', 'lower'])
+def test_apply_keyword_case(operator, case):
+    query = (f'select * from Departments d {operator} '
+             'dbo.GetReports(d.DeptMgrID) r')
+    convert = str.upper if case == 'upper' else str.lower
+    expected = (f'{convert("select")} * {convert("from")} Departments d '
+                f'{convert(operator)} dbo.GetReports(d.DeptMgrID) r')
+    assert sqlparse.format(query, keyword_case=case) == expected.replace('\r\n', '\n')
+
+
+@pytest.mark.parametrize('name', ['apply_column', 'apply2', 'apply$column',
+                                  'apply#column'])
+@pytest.mark.parametrize('prefix', ['cross', 'outer'])
+def test_apply_name_boundary(prefix, name):
+    assert list(lexer.tokenize(f'{prefix} {name}')) == [
+        (T.Keyword, prefix), (T.Whitespace, ' '), (T.Name, name),
+    ]
+
+
+@pytest.mark.parametrize('expression', [
+    'apply', 'cross_apply', 'outer_apply', 'apply(1)',
+    '"cross apply"', '[outer apply]', '`cross apply`',
+    "'outer apply'", '$$cross apply$$',
+])
+def test_apply_identifiers_and_quoted_text(expression):
+    query = f'select {expression} from t'
+    assert sqlparse.format(query, keyword_case='upper') == (
+        f'SELECT {expression} FROM t')