diff --git a/doc/source/whatsnew/v1.3.0.rst b/doc/source/whatsnew/v1.3.0.rst
index ff11ebc022ffb..3885d3ab6e794 100644
--- a/doc/source/whatsnew/v1.3.0.rst
+++ b/doc/source/whatsnew/v1.3.0.rst
@@ -234,6 +234,7 @@ Datetimelike
 - Bug in :meth:`DatetimeIndex.intersection`, :meth:`DatetimeIndex.symmetric_difference`, :meth:`PeriodIndex.intersection`, :meth:`PeriodIndex.symmetric_difference` always returning object-dtype when operating with :class:`CategoricalIndex` (:issue:`38741`)
 - Bug in :meth:`Series.where` incorrectly casting ``datetime64`` values to ``int64`` (:issue:`37682`)
 - Bug in :class:`Categorical` incorrectly typecasting ``datetime`` object to ``Timestamp`` (:issue:`38878`)
+- Bug in comparisons between :class:`Timestamp` object and ``datetime64`` objects just outside the implementation bounds for nanosecond ``datetime64`` (:issue:`39221`)
 - Bug in :meth:`Timestamp.round`, :meth:`Timestamp.floor`, :meth:`Timestamp.ceil` for values near the implementation bounds of :class:`Timestamp` (:issue:`39244`)
 - Bug in :func:`date_range` incorrectly creating :class:`DatetimeIndex` containing ``NaT`` instead of raising ``OutOfBoundsDatetime`` in corner cases (:issue:`24124`)
 
diff --git a/pandas/_libs/tslibs/timestamps.pyx b/pandas/_libs/tslibs/timestamps.pyx
index a630cad63ce70..1df589073a6ba 100644
--- a/pandas/_libs/tslibs/timestamps.pyx
+++ b/pandas/_libs/tslibs/timestamps.pyx
@@ -27,7 +27,16 @@ from cpython.datetime cimport (  # alias bc `tzinfo` is a kwarg below
     time,
     tzinfo as tzinfo_type,
 )
-from cpython.object cimport Py_EQ, Py_NE, PyObject_RichCompare, PyObject_RichCompareBool
+from cpython.object cimport (
+    Py_EQ,
+    Py_GE,
+    Py_GT,
+    Py_LE,
+    Py_LT,
+    Py_NE,
+    PyObject_RichCompare,
+    PyObject_RichCompareBool,
+)
 
 PyDateTime_IMPORT
 
@@ -295,6 +304,9 @@ cdef class _Timestamp(ABCTimestamp):
             try:
                 ots = type(self)(other)
             except ValueError:
+                if is_datetime64_object(other):
+                    # cast non-nano dt64 to pydatetime
+                    other = other.astype(object)
                 return self._compare_outside_nanorange(other, op)
 
         elif is_array(other):
@@ -349,12 +361,23 @@ cdef class _Timestamp(ABCTimestamp):
     cdef bint _compare_outside_nanorange(_Timestamp self, datetime other,
                                          int op) except -1:
         cdef:
-            datetime dtval = self.to_pydatetime()
+            datetime dtval = self.to_pydatetime(warn=False)
 
         if not self._can_compare(other):
             return NotImplemented
 
-        return PyObject_RichCompareBool(dtval, other, op)
+        if self.nanosecond == 0:
+            return PyObject_RichCompareBool(dtval, other, op)
+
+        # otherwise we have dtval < self
+        if op == Py_NE:
+            return True
+        if op == Py_EQ:
+            return False
+        if op == Py_LE or op == Py_LT:
+            return other.year <= self.year
+        if op == Py_GE or op == Py_GT:
+            return other.year >= self.year
 
     cdef bint _can_compare(self, datetime other):
         if self.tzinfo is not None:
diff --git a/pandas/tests/scalar/timestamp/test_comparisons.py b/pandas/tests/scalar/timestamp/test_comparisons.py
index 285733dc2c7af..9ee7cb1840e5b 100644
--- a/pandas/tests/scalar/timestamp/test_comparisons.py
+++ b/pandas/tests/scalar/timestamp/test_comparisons.py
@@ -1,4 +1,4 @@
-from datetime import datetime
+from datetime import datetime, timedelta
 import operator
 
 import numpy as np
@@ -244,6 +244,25 @@ def test_timestamp_compare_with_early_datetime(self):
         assert stamp < datetime(2700, 1, 1)
         assert stamp <= datetime(2700, 1, 1)
 
+        other = Timestamp.min.to_pydatetime(warn=False)
+        assert other - timedelta(microseconds=1) < Timestamp.min
+
+    def test_timestamp_compare_oob_dt64(self):
+        us = np.timedelta64(1, "us")
+        other = np.datetime64(Timestamp.min).astype("M8[us]")
+
+        # This may change if the implementation bound is dropped to match
+        #  DatetimeArray/DatetimeIndex GH#24124
+        assert Timestamp.min > other
+        # Note: numpy gets the reversed comparison wrong
+
+        other = np.datetime64(Timestamp.max).astype("M8[us]")
+        assert Timestamp.max > other  # not actually OOB
+        assert other < Timestamp.max
+
+        assert Timestamp.max < other + us
+        # Note: numpy gets the reversed comparison wrong
+
     def test_compare_zerodim_array(self):
         # GH#26916
         ts = Timestamp.now()