diff --git a/bindings/pydrake/BUILD.bazel b/bindings/pydrake/BUILD.bazel
index c1c873bde91d..28caf4094098 100644
--- a/bindings/pydrake/BUILD.bazel
+++ b/bindings/pydrake/BUILD.bazel
@@ -227,7 +227,7 @@ drake_py_test(
 )
 
 drake_py_test(
-    name = "math_test",
+    name = "test/math_test",
     size = "small",
     srcs = ["test/math_test.py"],
     main = "test/math_test.py",
@@ -236,6 +236,11 @@ drake_py_test(
     ],
 )
 
+alias(
+    name = "math_test",
+    actual = "test/math_test",
+)
+
 drake_py_test(
     name = "symbolic_variables_test",
     size = "small",
diff --git a/bindings/pydrake/systems/BUILD.bazel b/bindings/pydrake/systems/BUILD.bazel
index 194ff56cdfa1..c8983987ae23 100644
--- a/bindings/pydrake/systems/BUILD.bazel
+++ b/bindings/pydrake/systems/BUILD.bazel
@@ -92,6 +92,7 @@ drake_pybind_library(
 drake_pybind_library(
     name = "controllers_py",
     cc_deps = [
+        "//bindings/pydrake/util:wrap_function",
         "//systems/controllers:dynamic_programming",
     ],
     cc_so_name = "controllers",
diff --git a/bindings/pydrake/systems/controllers_py.cc b/bindings/pydrake/systems/controllers_py.cc
index d5c48e2bcca9..fbceecbb5e43 100644
--- a/bindings/pydrake/systems/controllers_py.cc
+++ b/bindings/pydrake/systems/controllers_py.cc
@@ -4,11 +4,34 @@
 #include <pybind11/stl.h>
 
 #include "drake/bindings/pydrake/pydrake_pybind.h"
+#include "drake/bindings/pydrake/util/wrap_function.h"
 #include "drake/systems/controllers/dynamic_programming.h"
 
 namespace drake {
 namespace pydrake {
 
+namespace {
+
+template <typename T, typename = void>
+struct wrap_ptr : public wrap_arg_default<T> {};
+
+template <typename T>
+struct wrap_ptr<const systems::Context<T>&> {
+  using Type = systems::Context<T>;
+  static auto wrap(const Type& arg) { return &arg; }
+  static auto unwrap(const Type* arg_wrapped) { return *arg_wrapped; }
+};
+
+// Ensures that `const Context<T>&` is wrapped with `const Context<T>*`.
+// TODO(eric.cousineau): Replace this with general wrappper, place in
+// `pydrake_pybind` or somewhere related.
+template <typename Func>
+auto WrapPtr(Func&& func) {
+  return WrapFunction<wrap_ptr>(std::forward<Func>(func));
+}
+
+}  // namespace
+
 PYBIND11_MODULE(controllers, m) {
   // NOLINTNEXTLINE(build/namespaces): Emulate placement in namespace.
   using namespace drake::systems::controllers;
@@ -21,7 +44,7 @@ PYBIND11_MODULE(controllers, m) {
       .def_readwrite("discount_factor",
                     &DynamicProgrammingOptions::discount_factor);
 
-  m.def("FittedValueIteration", &FittedValueIteration);
+  m.def("FittedValueIteration", WrapPtr(&FittedValueIteration));
 }
 
 }  // namespace pydrake