diff --git a/pandas/core/arrays/numpy_.py b/pandas/core/arrays/numpy_.py
index c9db995319cdf..6e4aa1a5efacf 100644
--- a/pandas/core/arrays/numpy_.py
+++ b/pandas/core/arrays/numpy_.py
@@ -23,6 +23,7 @@
 )
 from pandas.core.arraylike import OpsMixin
 from pandas.core.arrays._mixins import NDArrayBackedExtensionArray
+from pandas.core.construction import ensure_wrapped_if_datetimelike
 from pandas.core.strings.object_array import ObjectStringArrayMixin
 
 
@@ -395,6 +396,7 @@ def _cmp_method(self, other, op):
             other = other._ndarray
 
         pd_op = ops.get_array_op(op)
+        other = ensure_wrapped_if_datetimelike(other)
         with np.errstate(all="ignore"):
             result = pd_op(self._ndarray, other)
 
diff --git a/pandas/core/ops/array_ops.py b/pandas/core/ops/array_ops.py
index ba9da8d648597..387d8b463b8b4 100644
--- a/pandas/core/ops/array_ops.py
+++ b/pandas/core/ops/array_ops.py
@@ -195,20 +195,17 @@ def arithmetic_op(left: ArrayLike, right: Any, op):
         Or a 2-tuple of these in the case of divmod or rdivmod.
     """
 
-    # NB: We assume that extract_array has already been called
-    #  on `left` and `right`.
+    # NB: We assume that extract_array and ensure_wrapped_if_datetimelike
+    #  has already been called on `left` and `right`.
     # We need to special-case datetime64/timedelta64 dtypes (e.g. because numpy
     # casts integer dtypes to timedelta64 when operating with timedelta64 - GH#22390)
-    lvalues = ensure_wrapped_if_datetimelike(left)
-    rvalues = ensure_wrapped_if_datetimelike(right)
-    rvalues = _maybe_upcast_for_op(rvalues, lvalues.shape)
+    right = _maybe_upcast_for_op(right, left.shape)
 
-    if should_extension_dispatch(lvalues, rvalues) or isinstance(rvalues, Timedelta):
+    if should_extension_dispatch(left, right) or isinstance(right, Timedelta):
         # Timedelta is included because numexpr will fail on it, see GH#31457
-        res_values = op(lvalues, rvalues)
-
+        res_values = op(left, right)
     else:
-        res_values = _na_arithmetic_op(lvalues, rvalues, op)
+        res_values = _na_arithmetic_op(left, right, op)
 
     return res_values
 
diff --git a/pandas/core/series.py b/pandas/core/series.py
index e19d521bda3df..85c30096b1001 100644
--- a/pandas/core/series.py
+++ b/pandas/core/series.py
@@ -100,6 +100,7 @@
 import pandas.core.common as com
 from pandas.core.construction import (
     create_series_with_explicit_dtype,
+    ensure_wrapped_if_datetimelike,
     extract_array,
     is_empty_data,
     sanitize_array,
@@ -2872,7 +2873,7 @@ def _binop(self, other: Series, func, level=None, fill_value=None):
         if not self.index.equals(other.index):
             this, other = self.align(other, level=level, join="outer", copy=False)
 
-        this_vals, other_vals = ops.fill_binop(this.values, other.values, fill_value)
+        this_vals, other_vals = ops.fill_binop(this._values, other._values, fill_value)
 
         with np.errstate(all="ignore"):
             result = func(this_vals, other_vals)
@@ -5313,6 +5314,7 @@ def _arith_method(self, other, op):
 
         lvalues = self._values
         rvalues = extract_array(other, extract_numpy=True, extract_range=True)
+        rvalues = ensure_wrapped_if_datetimelike(rvalues)
 
         with np.errstate(all="ignore"):
             result = ops.arithmetic_op(lvalues, rvalues, op)