diff --git a/Misc/NEWS.d/next/Core and Builtins/2022-02-01-01-17-28.bpo-45885.CjyNf_.rst b/Misc/NEWS.d/next/Core and Builtins/2022-02-01-01-17-28.bpo-45885.CjyNf_.rst
new file mode 100644
index 00000000000000..6395bd1f18d5e1
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2022-02-01-01-17-28.bpo-45885.CjyNf_.rst	
@@ -0,0 +1 @@
+Added more fined-grained specialization failure stats regarding the ``COMPARE_OP`` bytecode.
\ No newline at end of file
diff --git a/Python/specialize.c b/Python/specialize.c
index aec94d9e60be41..b3793eead89352 100644
--- a/Python/specialize.c
+++ b/Python/specialize.c
@@ -533,6 +533,14 @@ initial_counter_value(void) {
 #define SPEC_FAIL_STRING_COMPARE 13
 #define SPEC_FAIL_NOT_FOLLOWED_BY_COND_JUMP 14
 #define SPEC_FAIL_BIG_INT 15
+#define SPEC_FAIL_COMPARE_BYTES 16
+#define SPEC_FAIL_COMPARE_TUPLE 17
+#define SPEC_FAIL_COMPARE_LIST 18
+#define SPEC_FAIL_COMPARE_SET 19
+#define SPEC_FAIL_COMPARE_BOOL 20
+#define SPEC_FAIL_COMPARE_BASEOBJECT 21
+#define SPEC_FAIL_COMPARE_FLOAT_LONG 22
+#define SPEC_FAIL_COMPARE_LONG_FLOAT 23
 
 static int
 specialize_module_load_attr(
@@ -1733,6 +1741,43 @@ _Py_Specialize_BinaryOp(PyObject *lhs, PyObject *rhs, _Py_CODEUNIT *instr,
     adaptive->counter = initial_counter_value();
 }
 
+
+#ifdef Py_STATS
+static int
+compare_op_fail_kind(PyObject *lhs, PyObject *rhs)
+{
+    if (Py_TYPE(lhs) != Py_TYPE(rhs)) {
+        if (PyFloat_CheckExact(lhs) && PyLong_CheckExact(rhs)) {
+            return SPEC_FAIL_COMPARE_FLOAT_LONG;
+        }
+        if (PyLong_CheckExact(lhs) && PyFloat_CheckExact(rhs)) {
+            return SPEC_FAIL_COMPARE_LONG_FLOAT;
+        }
+        return SPEC_FAIL_DIFFERENT_TYPES;
+    }
+    if (PyBytes_CheckExact(lhs)) {
+        return SPEC_FAIL_COMPARE_BYTES;
+    }
+    if (PyTuple_CheckExact(lhs)) {
+        return SPEC_FAIL_COMPARE_TUPLE;
+    }
+    if (PyList_CheckExact(lhs)) {
+        return SPEC_FAIL_COMPARE_LIST;
+    }
+    if (PySet_CheckExact(lhs) || PyFrozenSet_CheckExact(lhs)) {
+        return SPEC_FAIL_COMPARE_SET;
+    }
+    if (PyBool_Check(lhs)) {
+        return SPEC_FAIL_COMPARE_BOOL;
+    }
+    if (Py_TYPE(lhs)->tp_richcompare == PyBaseObject_Type.tp_richcompare) {
+        return SPEC_FAIL_COMPARE_BASEOBJECT;
+    }
+    return SPEC_FAIL_OTHER;
+}
+#endif
+
+
 static int compare_masks[] = {
     // 1-bit: jump if less than
     // 2-bit: jump if equal
@@ -1764,7 +1809,7 @@ _Py_Specialize_CompareOp(PyObject *lhs, PyObject *rhs,
         when_to_jump_mask = (1 | 2 | 4) & ~when_to_jump_mask;
     }
     if (Py_TYPE(lhs) != Py_TYPE(rhs)) {
-        SPECIALIZATION_FAIL(COMPARE_OP, SPEC_FAIL_DIFFERENT_TYPES);
+        SPECIALIZATION_FAIL(COMPARE_OP, compare_op_fail_kind(lhs, rhs));
         goto failure;
     }
     if (PyFloat_CheckExact(lhs)) {
@@ -1794,7 +1839,7 @@ _Py_Specialize_CompareOp(PyObject *lhs, PyObject *rhs,
             goto success;
         }
     }
-    SPECIALIZATION_FAIL(COMPARE_OP, SPEC_FAIL_OTHER);
+    SPECIALIZATION_FAIL(COMPARE_OP, compare_op_fail_kind(lhs, rhs));
 failure:
     STAT_INC(COMPARE_OP, failure);
     cache_backoff(adaptive);