diff -r f4a7e738ad24 Lib/distutils/tests/test_version.py
--- a/Lib/distutils/tests/test_version.py	Mon May 28 17:01:17 2012 +0100
+++ b/Lib/distutils/tests/test_version.py	Sun Jun 03 17:33:36 2012 +0200
@@ -55,7 +55,10 @@
                     ('3.2.pl0', '3.1.1.6', 1),
                     ('2g6', '11g', -1),
                     ('0.960923', '2.2beta29', -1),
-                    ('1.13++', '5.5.kw', -1))
+                    ('1.13++', '5.5.kw', -1),
+                    ('a.12.b.c', 'a.b.3', -1),
+                    ('1.0', '1', 1),
+                    ('1', '1.0', -1))
 
 
         for v1, v2, wanted in versions:
diff -r f4a7e738ad24 Lib/distutils/version.py
--- a/Lib/distutils/version.py	Mon May 28 17:01:17 2012 +0100
+++ b/Lib/distutils/version.py	Sun Jun 03 17:33:36 2012 +0200
@@ -28,6 +28,8 @@
 
 import re
 
+from itertools import zip_longest
+
 class Version:
     """Abstract base class for version numbering classes.  Just provides
     constructor (__init__) and reproducer (__repr__), because those
@@ -338,12 +340,16 @@
         if isinstance(other, str):
             other = LooseVersion(other)
 
-        if self.version == other.version:
-            return 0
-        if self.version < other.version:
-            return -1
-        if self.version > other.version:
-            return 1
-
+        for i, j in zip_longest(self.version, other.version, fillvalue=''):
+            if type(i) != type(j):
+                i = str(i)
+                j = str(j)
+            if i == j:
+                continue
+            elif i < j:
+                return -1
+            else:  # i > j
+                return 1
+        return 0
 
 # end class LooseVersion