diff --git a/src/packaging/specifiers.py b/src/packaging/specifiers.py
index 8f1e181f..ba8fe37b 100644
--- a/src/packaging/specifiers.py
+++ b/src/packaging/specifiers.py
@@ -399,7 +399,9 @@ def _compare_equal(self, prospective: Version, spec: str) -> bool:
         # We need special logic to handle prefix matching
         if spec.endswith(".*"):
             # In the case of prefix matching we want to ignore local segment.
-            normalized_prospective = canonicalize_version(prospective.public)
+            normalized_prospective = canonicalize_version(
+                prospective.public, strip_trailing_zero=False
+            )
             # Get the normalized version string ignoring the trailing .*
             normalized_spec = canonicalize_version(spec[:-2], strip_trailing_zero=False)
             # Split the spec out by dots, and pretend that there is an implicit
diff --git a/tests/test_specifiers.py b/tests/test_specifiers.py
index 104fac9b..799f873a 100644
--- a/tests/test_specifiers.py
+++ b/tests/test_specifiers.py
@@ -369,6 +369,8 @@ def test_comparison_non_specifier(self):
                 ("2!1.0", "==2!1.*"),
                 ("2!1.0", "==2!1.0"),
                 ("2!1.0", "!=1.0"),
+                ("2!1.0.0", "==2!1.0.*"),
+                ("2!1.0.0", "==2!1.*"),
                 ("1.0", "!=2!1.0"),
                 ("1.0", "<=2!0.1"),
                 ("2!1.0", ">=2.0"),