diff --git a/src/poetry/core/version/markers.py b/src/poetry/core/version/markers.py
index a5f50cf2c..e9db59266 100644
--- a/src/poetry/core/version/markers.py
+++ b/src/poetry/core/version/markers.py
@@ -21,6 +21,7 @@
 from poetry.core.constraints.generic import UnionConstraint
 from poetry.core.constraints.generic.parser import STR_CMP_CONSTRAINT
 from poetry.core.constraints.version import VersionConstraint
+from poetry.core.constraints.version import VersionRange
 from poetry.core.constraints.version import VersionUnion
 from poetry.core.constraints.version.exceptions import ParseConstraintError
 from poetry.core.version.grammars import GRAMMAR_PEP_508_MARKERS
@@ -446,10 +447,15 @@ def reduce_by_python_constraint(
         self, python_constraint: VersionConstraint
     ) -> BaseMarker:
         if self.name in PYTHON_VERSION_MARKERS:
+            from poetry.core.packages.utils.utils import (
+                get_python_constraint_from_marker,
+            )
+
             assert isinstance(self._constraint, VersionConstraint)
-            if self._constraint.allows_all(python_constraint):
+            constraint = get_python_constraint_from_marker(self)
+            if constraint.allows_all(python_constraint):
                 return AnyMarker()
-            elif not self._constraint.allows_any(python_constraint):
+            elif not constraint.allows_any(python_constraint):
                 return EmptyMarker()
 
         return self
@@ -931,7 +937,7 @@ def reduce_by_python_constraint(
         from poetry.core.packages.utils.utils import get_python_constraint_from_marker
 
         markers: Iterable[BaseMarker] = self._markers
-        if isinstance(python_constraint, VersionUnion):
+        if isinstance(python_constraint, (VersionRange, VersionUnion)):
             python_only_markers = []
             other_markers = []
             for m in self._markers:
diff --git a/tests/version/test_markers.py b/tests/version/test_markers.py
index 280eecbab..4e1ea27a9 100644
--- a/tests/version/test_markers.py
+++ b/tests/version/test_markers.py
@@ -1439,7 +1439,12 @@ def test_only(marker: str, only: list[str], expected: str) -> None:
         ("<empty>", "~3.8", "<empty>"),
         ('sys_platform == "linux"', "~3.8", 'sys_platform == "linux"'),
         ('python_version >= "3.8"', "~3.8", ""),
-        ('python_version > "3.8"', "~3.8", 'python_version > "3.8"'),
+        ('python_version == "3.8"', ">=3.8.7,<3.9.0", ""),
+        ('python_version == "3.8" or python_version >= "3.9"', ">=3.8.0,<4.0.0", ""),
+        ('python_version == "3.8" or python_version >= "3.9"', ">=3.8.7,<4.0.0", ""),
+        ('python_version > "3.7"', "~3.8", ""),
+        ('python_version > "3.8"', "~3.8", "<empty>"),
+        ('python_version >= "3.8"', "~3.8", ""),
         ('python_version >= "3.9"', "~3.8", "<empty>"),
         ('python_full_version >= "3.8.0"', "~3.8", ""),
         ('python_full_version >= "3.8.1"', "~3.8", 'python_full_version >= "3.8.1"'),
@@ -1503,6 +1508,16 @@ def test_only(marker: str, only: list[str], expected: str) -> None:
             "~3.7 || ~3.9",
             'sys_platform == "linux" or sys_platform == "win32"',
         ),
+        (
+            'python_version == "3.8" or sys_platform == "linux" or python_version >= "3.9"',
+            ">=3.8.0,<4.0.0",
+            'sys_platform == "linux"',
+        ),
+        (
+            'python_version == "3.8" or sys_platform == "linux" or python_version >= "3.9"',
+            ">=3.8.7,<4.0.0",
+            'sys_platform == "linux"',
+        ),
     ],
 )
 def test_reduce_by_python_constraint(