diff --git a/IPython/terminal/interactiveshell.py b/IPython/terminal/interactiveshell.py
index 5c79a17..98e5eb8 100644
--- a/IPython/terminal/interactiveshell.py
+++ b/IPython/terminal/interactiveshell.py
@@ -188,6 +188,15 @@ class TerminalInteractiveShell(InteractiveShell):
         allow_none=True
     ).tag(config=True)
 
+    auto_match = Bool(
+        False,
+        help="""
+        Automatically add/delete closing bracket or quote when opening bracket or quote is entered/deleted.
+        Brackets: (), [], {}
+        Quotes: '', \"\"
+        """,
+    ).tag(config=True)
+
     mouse_support = Bool(False,
         help="Enable mouse support in the prompt\n(Note: prevents selecting text with the mouse)"
     ).tag(config=True)
diff --git a/IPython/terminal/shortcuts.py b/IPython/terminal/shortcuts.py
index 75faaa5..6aab3d2 100644
--- a/IPython/terminal/shortcuts.py
+++ b/IPython/terminal/shortcuts.py
@@ -85,12 +85,169 @@ def create_ipython_shortcuts(shell):
 
     kb.add('f2', filter=has_focus(DEFAULT_BUFFER))(open_input_in_editor)
 
-    if shell.display_completions == 'readlinelike':
-        kb.add('c-i', filter=(has_focus(DEFAULT_BUFFER)
-                              & ~has_selection
-                              & insert_mode
-                              & ~cursor_in_leading_ws
-                        ))(display_completions_like_readline)
+    @Condition
+    def auto_match():
+        return shell.auto_match
+
+    focused_insert = (vi_insert_mode | emacs_insert_mode) & has_focus(DEFAULT_BUFFER)
+    _preceding_text_cache = {}
+    _following_text_cache = {}
+
+    def preceding_text(pattern):
+        try:
+            return _preceding_text_cache[pattern]
+        except KeyError:
+            pass
+        m = re.compile(pattern)
+
+        def _preceding_text():
+            app = get_app()
+            return bool(m.match(app.current_buffer.document.current_line_before_cursor))
+
+        condition = Condition(_preceding_text)
+        _preceding_text_cache[pattern] = condition
+        return condition
+
+    def following_text(pattern):
+        try:
+            return _following_text_cache[pattern]
+        except KeyError:
+            pass
+        m = re.compile(pattern)
+
+        def _following_text():
+            app = get_app()
+            return bool(m.match(app.current_buffer.document.current_line_after_cursor))
+
+        condition = Condition(_following_text)
+        _following_text_cache[pattern] = condition
+        return condition
+
+    # auto match
+    @kb.add("(", filter=focused_insert & auto_match & following_text(r"[,)}\]]|$"))
+    def _(event):
+        event.current_buffer.insert_text("()")
+        event.current_buffer.cursor_left()
+
+    @kb.add("[", filter=focused_insert & auto_match & following_text(r"[,)}\]]|$"))
+    def _(event):
+        event.current_buffer.insert_text("[]")
+        event.current_buffer.cursor_left()
+
+    @kb.add("{", filter=focused_insert & auto_match & following_text(r"[,)}\]]|$"))
+    def _(event):
+        event.current_buffer.insert_text("{}")
+        event.current_buffer.cursor_left()
+
+    @kb.add('"', filter=focused_insert & auto_match & following_text(r"[,)}\]]|$"))
+    def _(event):
+        event.current_buffer.insert_text('""')
+        event.current_buffer.cursor_left()
+
+    @kb.add("'", filter=focused_insert & auto_match & following_text(r"[,)}\]]|$"))
+    def _(event):
+        event.current_buffer.insert_text("''")
+        event.current_buffer.cursor_left()
+
+    # raw string
+    @kb.add("(", filter=focused_insert & preceding_text(r".*(r|R)[\"'](-*)$"))
+    def _(event):
+        matches = re.match(
+            r".*(r|R)[\"'](-*)",
+            event.current_buffer.document.current_line_before_cursor,
+        )
+        dashes = matches.group(2) or ""
+        event.current_buffer.insert_text("()" + dashes)
+        event.current_buffer.cursor_left(len(dashes) + 1)
+
+    @kb.add("[", filter=focused_insert & preceding_text(r".*(r|R)[\"'](-*)$"))
+    def _(event):
+        matches = re.match(
+            r".*(r|R)[\"'](-*)",
+            event.current_buffer.document.current_line_before_cursor,
+        )
+        dashes = matches.group(2) or ""
+        event.current_buffer.insert_text("[]" + dashes)
+        event.current_buffer.cursor_left(len(dashes) + 1)
+
+    @kb.add("{", filter=focused_insert & preceding_text(r".*(r|R)[\"'](-*)$"))
+    def _(event):
+        matches = re.match(
+            r".*(r|R)[\"'](-*)",
+            event.current_buffer.document.current_line_before_cursor,
+        )
+        dashes = matches.group(2) or ""
+        event.current_buffer.insert_text("{}" + dashes)
+        event.current_buffer.cursor_left(len(dashes) + 1)
+
+    @kb.add('"', filter=focused_insert & preceding_text(r".*(r|R)$"))
+    def _(event):
+        event.current_buffer.insert_text('""')
+        event.current_buffer.cursor_left()
+
+    @kb.add("'", filter=focused_insert & preceding_text(r".*(r|R)$"))
+    def _(event):
+        event.current_buffer.insert_text("''")
+        event.current_buffer.cursor_left()
+
+    # just move cursor
+    @kb.add(")", filter=focused_insert & auto_match & following_text(r"^\)"))
+    @kb.add("]", filter=focused_insert & auto_match & following_text(r"^\]"))
+    @kb.add("}", filter=focused_insert & auto_match & following_text(r"^\}"))
+    @kb.add('"', filter=focused_insert & auto_match & following_text('^"'))
+    @kb.add("'", filter=focused_insert & auto_match & following_text("^'"))
+    def _(event):
+        event.current_buffer.cursor_right()
+
+    @kb.add(
+        "backspace",
+        filter=focused_insert
+        & preceding_text(r".*\($")
+        & auto_match
+        & following_text(r"^\)"),
+    )
+    @kb.add(
+        "backspace",
+        filter=focused_insert
+        & preceding_text(r".*\[$")
+        & auto_match
+        & following_text(r"^\]"),
+    )
+    @kb.add(
+        "backspace",
+        filter=focused_insert
+        & preceding_text(r".*\{$")
+        & auto_match
+        & following_text(r"^\}"),
+    )
+    @kb.add(
+        "backspace",
+        filter=focused_insert
+        & preceding_text('.*"$')
+        & auto_match
+        & following_text('^"'),
+    )
+    @kb.add(
+        "backspace",
+        filter=focused_insert
+        & preceding_text(r".*'$")
+        & auto_match
+        & following_text(r"^'"),
+    )
+    def _(event):
+        event.current_buffer.delete()
+        event.current_buffer.delete_before_cursor()
+
+    if shell.display_completions == "readlinelike":
+        kb.add(
+            "c-i",
+            filter=(
+                has_focus(DEFAULT_BUFFER)
+                & ~has_selection
+                & insert_mode
+                & ~cursor_in_leading_ws
+            ),
+        )(display_completions_like_readline)
 
     if sys.platform == "win32":
         kb.add("c-v", filter=(has_focus(DEFAULT_BUFFER) & ~vi_mode))(win_paste)