diff --git a/changelog.d/fixed/glob.md b/changelog.d/fixed/glob.md
new file mode 100644
index 000000000..dac4d9525
--- /dev/null
+++ b/changelog.d/fixed/glob.md
@@ -0,0 +1,2 @@
+- Fixed the globbing of a single asterisk succeeded by a slash (e.g.
+  `directory-*/foo.py`). The glob previously did nothing. (#1078)
diff --git a/src/reuse/global_licensing.py b/src/reuse/global_licensing.py
index 3ca566578..18fef001f 100644
--- a/src/reuse/global_licensing.py
+++ b/src/reuse/global_licensing.py
@@ -352,6 +352,7 @@ class AnnotationsItem:
 
     def __attrs_post_init__(self) -> None:
         def translate(path: str) -> str:
+            # pylint: disable=too-many-branches
             blocks = []
             escaping = False
             globstar = False
@@ -360,7 +361,7 @@ def translate(path: str) -> str:
                 if char == "\\":
                     if prev_char == "\\" and escaping:
                         escaping = False
-                        blocks.append(r"\\")
+                        blocks.append("\\\\")
                     else:
                         escaping = True
                 elif char == "*":
@@ -372,6 +373,8 @@ def translate(path: str) -> str:
                         blocks.append(r".*")
                 elif char == "/":
                     if not globstar:
+                        if prev_char == "*":
+                            blocks.append("[^/]*")
                         blocks.append("/")
                     escaping = False
                 else:
diff --git a/tests/test_global_licensing.py b/tests/test_global_licensing.py
index 2a415426f..175623916 100644
--- a/tests/test_global_licensing.py
+++ b/tests/test_global_licensing.py
@@ -257,6 +257,11 @@ def test_asterisk_asterisk(self):
         assert item.matches("src/foo.py")
         assert item.matches(".foo/bar")
 
+    def test_asterisk_slash(self):
+        """Handle asterisk slash."""
+        item = AnnotationsItem(paths=[r"*/file"])
+        assert item.matches("foo/file")
+
     def test_escape_asterisk(self):
         """Handle escape asterisk."""
         item = AnnotationsItem(paths=[r"\*.py"])
@@ -293,6 +298,7 @@ def test_escape_escape_asterisk(self):
         """Handle escape escape asterisk."""
         item = AnnotationsItem(paths=[r"\\*.py"])
         assert item.matches(r"\foo.py")
+        assert not item.matches(r"foo.py")
 
     def test_asterisk_asterisk_asterisk(self):
         """Handle asterisk asterisk asterisk."""