diff --git a/src/calibre/ebooks/oeb/polish/toc.py b/src/calibre/ebooks/oeb/polish/toc.py
index 1da902a1b7..7f119b2556 100644
--- a/src/calibre/ebooks/oeb/polish/toc.py
+++ b/src/calibre/ebooks/oeb/polish/toc.py
@@ -45,6 +45,16 @@ class TOC(object):
         self.children.remove(child)
         child.parent = None
 
+    def remove_from_parent(self):
+        if self.parent is None:
+            return
+        idx = self.parent.children.index(self)
+        for child in reversed(self.children):
+            child.parent = self.parent
+            self.parent.children.insert(idx, child)
+        self.parent.children.remove(self)
+        self.parent = None
+
     def __iter__(self):
         for c in self.children:
             yield c
@@ -407,3 +417,18 @@ def commit_toc(container, toc, lang=None, uid=None):
     container.replace(tocname, root)
     container.pretty_print.add(tocname)
 
+def remove_names_from_toc(container, names):
+    toc = get_toc(container)
+    if len(toc) == 0:
+        return False
+    remove = []
+    names = frozenset(names)
+    for node in toc.iterdescendants():
+        if node.dest in names:
+            remove.append(node)
+    if remove:
+        for node in reversed(remove):
+            node.remove_from_parent()
+        commit_toc(container, toc)
+        return True
+    return False
diff --git a/src/calibre/gui2/tweak_book/boss.py b/src/calibre/gui2/tweak_book/boss.py
index 1502e3de4e..eca91db1e6 100644
--- a/src/calibre/gui2/tweak_book/boss.py
+++ b/src/calibre/gui2/tweak_book/boss.py
@@ -23,6 +23,7 @@ from calibre.ebooks.oeb.polish.cover import mark_as_cover, mark_as_titlepage
 from calibre.ebooks.oeb.polish.pretty import fix_all_html, pretty_all
 from calibre.ebooks.oeb.polish.replace import rename_files, replace_file
 from calibre.ebooks.oeb.polish.split import split, merge, AbortError
+from calibre.ebooks.oeb.polish.toc import remove_names_from_toc
 from calibre.gui2 import error_dialog, choose_files, question_dialog, info_dialog, choose_save_file
 from calibre.gui2.dialogs.confirm_delete import confirm
 from calibre.gui2.tweak_book import set_current_container, current_container, tprefs, actions, editors
@@ -257,11 +258,14 @@ class Boss(QObject):
             c.remove_item(name)
         self.set_modified()
         self.gui.file_list.delete_done(spine_items, other_items)
-        for name in [x for x, remove in spine_items if remove] + list(other_items):
+        spine_names = [x for x, remove in spine_items if remove]
+        for name in spine_names + list(other_items):
             if name in editors:
                 self.close_editor(name)
         if not editors:
             self.gui.preview.clear()
+        if remove_names_from_toc(current_container(), spine_names + list(other_items)):
+            self.gui.toc_view.update_if_visible()
 
     def commit_dirty_opf(self):
         c = current_container()