diff --git a/Doc/library/ensurepip.rst b/Doc/library/ensurepip.rst
index fa102c4a080103..26cf1715f5d74b 100644
--- a/Doc/library/ensurepip.rst
+++ b/Doc/library/ensurepip.rst
@@ -61,7 +61,11 @@ is at least as recent as the one available in ``ensurepip``, pass the
 By default, ``pip`` is installed into the current virtual environment
 (if one is active) or into the system site packages (if there is no
 active virtual environment). The installation location can be controlled
-through two additional command line options:
+through some additional command line options:
+
+.. option:: --prefix <dir>
+
+   Installs ``pip`` using the given directory prefix.
 
 .. option:: --root <dir>
 
@@ -104,7 +108,7 @@ Module API
 
 .. function:: bootstrap(root=None, upgrade=False, user=False, \
                         altinstall=False, default_pip=False, \
-                        verbosity=0)
+                        verbosity=0, prefix=None)
 
    Bootstraps ``pip`` into the current or designated environment.
 
@@ -132,6 +136,12 @@ Module API
    *verbosity* controls the level of output to :data:`sys.stdout` from the
    bootstrapping operation.
 
+   *prefix* specifies the directory prefix to use when installing.
+
+   .. versionadded:: 3.14
+
+      The *prefix* parameter.
+
    .. audit-event:: ensurepip.bootstrap root ensurepip.bootstrap
 
    .. note::
diff --git a/Lib/ensurepip/__init__.py b/Lib/ensurepip/__init__.py
index aa641e94a8b336..2d41dd09d9d9da 100644
--- a/Lib/ensurepip/__init__.py
+++ b/Lib/ensurepip/__init__.py
@@ -108,25 +108,25 @@ def _disable_pip_configuration_settings():
 
 def bootstrap(*, root=None, upgrade=False, user=False,
               altinstall=False, default_pip=False,
-              verbosity=0):
+              verbosity=0, prefix=None):
     """
     Bootstrap pip into the current Python installation (or the given root
-    directory).
+    and directory prefix).
 
     Note that calling this function will alter both sys.path and os.environ.
     """
     # Discard the return value
     _bootstrap(root=root, upgrade=upgrade, user=user,
                altinstall=altinstall, default_pip=default_pip,
-               verbosity=verbosity)
+               verbosity=verbosity, prefix=prefix)
 
 
 def _bootstrap(*, root=None, upgrade=False, user=False,
               altinstall=False, default_pip=False,
-              verbosity=0):
+              verbosity=0, prefix=None):
     """
     Bootstrap pip into the current Python installation (or the given root
-    directory). Returns pip command status code.
+    and directory prefix). Returns pip command status code.
 
     Note that calling this function will alter both sys.path and os.environ.
     """
@@ -160,15 +160,31 @@ def _bootstrap(*, root=None, upgrade=False, user=False,
 
         # Construct the arguments to be passed to the pip command
         args = ["install", "--no-cache-dir", "--no-index", "--find-links", tmpdir]
-        if root:
-            args += ["--root", root]
         if upgrade:
             args += ["--upgrade"]
-        if user:
-            args += ["--user"]
         if verbosity:
             args += ["-" + "v" * verbosity]
 
+        if user:
+            # --user is mutually exclusive with --root/--prefix,
+            # pip will enforce this.
+            args += ["--user"]
+        else:
+            # Handle installation paths.
+            # If --root is given but not --prefix, we default to a prefix of "/"
+            # so that the install happens at the root of the --root directory.
+            # Otherwise, pip would use the configured sys.prefix, e.g.
+            # /usr/local, and install into ${root}/usr/local/.
+            effective_prefix = prefix
+            if root and not prefix:
+                effective_prefix = "/"
+
+            if root:
+                args += ["--root", root]
+
+            if effective_prefix:
+                args += ["--prefix", effective_prefix]
+
         return _run_pip([*args, "pip"], [os.fsdecode(tmp_wheel_path)])
 
 
@@ -237,6 +253,11 @@ def _main(argv=None):
         default=None,
         help="Install everything relative to this alternate root directory.",
     )
+    parser.add_argument(
+        "--prefix",
+        default=None,
+        help="Install everything using this prefix.",
+    )
     parser.add_argument(
         "--altinstall",
         action="store_true",
@@ -256,6 +277,7 @@ def _main(argv=None):
 
     return _bootstrap(
         root=args.root,
+        prefix=args.prefix,
         upgrade=args.upgrade,
         user=args.user,
         verbosity=args.verbosity,
diff --git a/Lib/test/test_ensurepip.py b/Lib/test/test_ensurepip.py
index 6d3c91b0b6d9f9..cd858ff09f3e4d 100644
--- a/Lib/test/test_ensurepip.py
+++ b/Lib/test/test_ensurepip.py
@@ -100,6 +100,21 @@ def test_bootstrapping_with_root(self):
             unittest.mock.ANY,
         )
 
+    def test_bootstrapping_with_prefix(self):
+        ensurepip.bootstrap(prefix="/foo/bar/")
+        self.run_pip.assert_called_once_with(
+            [
+                "install", "--no-cache-dir", "--no-index", "--find-links",
+                unittest.mock.ANY, "--prefix", "/foo/bar/", "pip",
+            ],
+            unittest.mock.ANY,
+        )
+
+    def test_root_and_prefix_mutual_exclusive(self):
+        with self.assertRaises(ValueError):
+            ensurepip.bootstrap(root="", prefix="")
+        self.assertFalse(self.run_pip.called)
+
     def test_bootstrapping_with_user(self):
         ensurepip.bootstrap(user=True)
 
diff --git a/Makefile.pre.in b/Makefile.pre.in
index 66b34b779f27cb..07bbd6c4dde729 100644
--- a/Makefile.pre.in
+++ b/Makefile.pre.in
@@ -2336,7 +2336,7 @@ install: @FRAMEWORKINSTALLFIRST@ @INSTALLTARGETS@ @FRAMEWORKINSTALLLAST@
 			install|*) ensurepip="" ;; \
 		esac; \
 		$(RUNSHARED) $(PYTHON_FOR_BUILD) -m ensurepip \
-			$$ensurepip --root=$(DESTDIR)/ ; \
+			$$ensurepip --prefix=$(prefix) ; \
 	fi
 
 .PHONY: altinstall
@@ -2347,7 +2347,7 @@ altinstall: commoninstall
 			install|*) ensurepip="--altinstall" ;; \
 		esac; \
 		$(RUNSHARED) $(PYTHON_FOR_BUILD) -m ensurepip \
-			$$ensurepip --root=$(DESTDIR)/ ; \
+			$$ensurepip --prefix=$(prefix) ; \
 	fi
 
 .PHONY: commoninstall
diff --git a/Misc/NEWS.d/next/Library/2019-12-16-17-50-42.bpo-31046.XA-Qfr.rst b/Misc/NEWS.d/next/Library/2019-12-16-17-50-42.bpo-31046.XA-Qfr.rst
new file mode 100644
index 00000000000000..07eb89d4d23e50
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2019-12-16-17-50-42.bpo-31046.XA-Qfr.rst
@@ -0,0 +1 @@
+A directory prefix can now be specified when using :mod:`ensurepip`.