diff --git a/src/librustdoc/clean/mod.rs b/src/librustdoc/clean/mod.rs
index 2c98cba90d718..25d224b9a7337 100644
--- a/src/librustdoc/clean/mod.rs
+++ b/src/librustdoc/clean/mod.rs
@@ -57,11 +57,43 @@ impl<'tcx> Clean<'tcx, Item> for DocModule<'tcx> {
                 .map(|(item, renamed)| clean_maybe_renamed_foreign_item(cx, item, *renamed)),
         );
         items.extend(self.mods.iter().map(|x| x.clean(cx)));
-        items.extend(
-            self.items
-                .iter()
-                .flat_map(|(item, renamed)| clean_maybe_renamed_item(cx, item, *renamed)),
-        );
+
+        // Split up imports from all other items.
+        //
+        // This covers the case where somebody does an import which should pull in an item,
+        // but there's already an item with the same namespace and same name. Rust gives
+        // priority to the not-imported one, so we should, too.
+        let mut inserted = FxHashSet::default();
+        items.extend(self.items.iter().flat_map(|(item, renamed)| {
+            // First, lower everything other than imports.
+            if matches!(item.kind, hir::ItemKind::Use(..)) {
+                return Vec::new();
+            }
+            let v = clean_maybe_renamed_item(cx, item, *renamed);
+            for item in &v {
+                if let Some(name) = item.name {
+                    inserted.insert((item.type_(), name));
+                }
+            }
+            v
+        }));
+        items.extend(self.items.iter().flat_map(|(item, renamed)| {
+            // Now we actually lower the imports, skipping everything else.
+            if !matches!(item.kind, hir::ItemKind::Use(..)) {
+                return Vec::new();
+            }
+            let mut v = clean_maybe_renamed_item(cx, item, *renamed);
+            v.drain_filter(|item| {
+                if let Some(name) = item.name {
+                    // If an item with the same type and name already exists,
+                    // it takes priority over the inlined stuff.
+                    !inserted.insert((item.type_(), name))
+                } else {
+                    false
+                }
+            });
+            v
+        }));
 
         // determine if we should display the inner contents or
         // the outer `mod` item for the source code.
diff --git a/src/test/rustdoc/auxiliary/issue-99221-aux.rs b/src/test/rustdoc/auxiliary/issue-99221-aux.rs
new file mode 100644
index 0000000000000..e061e42b29db8
--- /dev/null
+++ b/src/test/rustdoc/auxiliary/issue-99221-aux.rs
@@ -0,0 +1,20 @@
+pub struct Option;
+impl Option {
+    pub fn unwrap(self) {}
+}
+
+mod macros {
+    use crate::Option;
+    /// [`Option::unwrap`]
+    #[macro_export]
+    macro_rules! print {
+        () => ()
+    }
+}
+
+mod structs {
+    use crate::Option;
+    /// [`Option::unwrap`]
+    pub struct Print;
+}
+pub use structs::Print;
diff --git a/src/test/rustdoc/issue-99221-multiple-macro-rules-w-same-name-submodule.rs b/src/test/rustdoc/issue-99221-multiple-macro-rules-w-same-name-submodule.rs
new file mode 100644
index 0000000000000..e74881d387dc1
--- /dev/null
+++ b/src/test/rustdoc/issue-99221-multiple-macro-rules-w-same-name-submodule.rs
@@ -0,0 +1,19 @@
+// aux-build:issue-99221-aux.rs
+// build-aux-docs
+// ignore-cross-compile
+
+#![crate_name = "foo"]
+
+#[macro_use]
+extern crate issue_99221_aux;
+
+pub use issue_99221_aux::*;
+
+// @count foo/index.html '//a[@class="macro"]' 1
+
+mod inner {
+    #[macro_export]
+    macro_rules! print {
+        () => ()
+    }
+}
diff --git a/src/test/rustdoc/issue-99221-multiple-macro-rules-w-same-name.rs b/src/test/rustdoc/issue-99221-multiple-macro-rules-w-same-name.rs
new file mode 100644
index 0000000000000..46d59654b99eb
--- /dev/null
+++ b/src/test/rustdoc/issue-99221-multiple-macro-rules-w-same-name.rs
@@ -0,0 +1,17 @@
+// aux-build:issue-99221-aux.rs
+// build-aux-docs
+// ignore-cross-compile
+
+#![crate_name = "foo"]
+
+#[macro_use]
+extern crate issue_99221_aux;
+
+pub use issue_99221_aux::*;
+
+// @count foo/index.html '//a[@class="macro"]' 1
+
+#[macro_export]
+macro_rules! print {
+    () => ()
+}
diff --git a/src/test/rustdoc/issue-99221-multiple-structs-w-same-name.rs b/src/test/rustdoc/issue-99221-multiple-structs-w-same-name.rs
new file mode 100644
index 0000000000000..41e64726a3246
--- /dev/null
+++ b/src/test/rustdoc/issue-99221-multiple-structs-w-same-name.rs
@@ -0,0 +1,14 @@
+// aux-build:issue-99221-aux.rs
+// build-aux-docs
+// ignore-cross-compile
+
+#![crate_name = "foo"]
+
+#[macro_use]
+extern crate issue_99221_aux;
+
+pub use issue_99221_aux::*;
+
+// @count foo/index.html '//a[@class="struct"][@title="foo::Print struct"]' 1
+
+pub struct Print;