diff --git a/ash/wm/overview/overview_item.cc b/ash/wm/overview/overview_item.cc
index ba562947062e57..e51f9575f0282a 100644
--- a/ash/wm/overview/overview_item.cc
+++ b/ash/wm/overview/overview_item.cc
@@ -329,6 +329,16 @@ void OverviewItem::EnsureVisible() {
 }
 
 void OverviewItem::Shutdown() {
+  // If `hide_windows` still manages the visibility of this overview item
+  // window, remove it from the list without showing.
+  ScopedOverviewHideWindows* hide_windows =
+      overview_session_->hide_windows_for_saved_desks_grid();
+  if (item_widget_ && hide_windows &&
+      hide_windows->HasWindow(item_widget_->GetNativeWindow())) {
+    hide_windows->RemoveWindow(item_widget_->GetNativeWindow(),
+                               /*show_window=*/false);
+  }
+
   item_widget_.reset();
   overview_item_view_ = nullptr;
 }
@@ -1486,13 +1496,16 @@ void OverviewItem::ShowWindowInOverview() {
   if (hide_windows->HasWindow(GetWindow())) {
     const bool ignore_activations = overview_session_->ignore_activations();
     overview_session_->set_ignore_activations(true);
-    hide_windows->RemoveWindow(GetWindow());
+    hide_windows->RemoveWindow(GetWindow(), /*show_window=*/true);
     overview_session_->set_ignore_activations(ignore_activations);
   }
 
   // Show the overview item window.
-  if (item_widget_ && hide_windows->HasWindow(item_widget_->GetNativeWindow()))
-    hide_windows->RemoveWindow(item_widget_->GetNativeWindow());
+  if (item_widget_ &&
+      hide_windows->HasWindow(item_widget_->GetNativeWindow())) {
+    hide_windows->RemoveWindow(item_widget_->GetNativeWindow(),
+                               /*show_window=*/true);
+  }
 }
 
 }  // namespace ash
diff --git a/ash/wm/overview/scoped_overview_hide_windows.cc b/ash/wm/overview/scoped_overview_hide_windows.cc
index b8bc893d16ed42..4a5ef97ee6bf74 100644
--- a/ash/wm/overview/scoped_overview_hide_windows.cc
+++ b/ash/wm/overview/scoped_overview_hide_windows.cc
@@ -43,10 +43,11 @@ void ScopedOverviewHideWindows::AddWindow(aura::Window* window) {
   window->Hide();
 }
 
-void ScopedOverviewHideWindows::RemoveWindow(aura::Window* window) {
+void ScopedOverviewHideWindows::RemoveWindow(aura::Window* window,
+                                             bool show_window) {
   DCHECK(HasWindow(window));
   window->RemoveObserver(this);
-  if (!window->is_destroying() && window_visibility_[window])
+  if (!window->is_destroying() && window_visibility_[window] && show_window)
     window->Show();
   window_visibility_.erase(window);
 }
@@ -57,7 +58,7 @@ void ScopedOverviewHideWindows::RemoveAllWindows() {
   for (const auto& element : window_visibility_)
     windows_to_remove.push_back(element.first);
   for (auto* window : base::Reversed(windows_to_remove))
-    RemoveWindow(window);
+    RemoveWindow(window, /*show_window=*/true);
 }
 
 void ScopedOverviewHideWindows::OnWindowDestroying(aura::Window* window) {
diff --git a/ash/wm/overview/scoped_overview_hide_windows.h b/ash/wm/overview/scoped_overview_hide_windows.h
index 5749e7416991a0..cf9d2ea7e06d6b 100644
--- a/ash/wm/overview/scoped_overview_hide_windows.h
+++ b/ash/wm/overview/scoped_overview_hide_windows.h
@@ -31,7 +31,7 @@ class ScopedOverviewHideWindows : public aura::WindowObserver {
 
   bool HasWindow(aura::Window* window) const;
   void AddWindow(aura::Window* window);
-  void RemoveWindow(aura::Window* window);
+  void RemoveWindow(aura::Window* window, bool show_window);
   void RemoveAllWindows();
 
   // aura::WindowObserver:
diff --git a/ash/wm/overview/scoped_overview_transform_window.cc b/ash/wm/overview/scoped_overview_transform_window.cc
index e9451f56b4d46b..6cedd0044c4004 100644
--- a/ash/wm/overview/scoped_overview_transform_window.cc
+++ b/ash/wm/overview/scoped_overview_transform_window.cc
@@ -600,7 +600,7 @@ void ScopedOverviewTransformWindow::OnWindowPropertyChanged(
   if (current_value) {
     AddHiddenTransientWindows({window});
   } else {
-    hidden_transient_children_->RemoveWindow(window);
+    hidden_transient_children_->RemoveWindow(window, /*show_window=*/true);
   }
 }