diff --git a/Library/Homebrew/cmd/bottle.rb b/Library/Homebrew/cmd/bottle.rb
index 83dd729c76..f868c00b90 100644
--- a/Library/Homebrew/cmd/bottle.rb
+++ b/Library/Homebrew/cmd/bottle.rb
@@ -24,10 +24,14 @@ module Homebrew extend self
     puts "  cellar '#{cellar}'" if bottle.cellar.to_s != '/usr/local/Cellar'
     puts "  revision #{bottle.revision}" if bottle.revision > 0
     Checksum::TYPES.each do |checksum_type|
-      checksum_cat = bottle.send checksum_type
-      next unless checksum_cat
-      checksum_cat.each do |cat, checksum|
-        puts "  #{checksum_type} '#{checksum}' => :#{cat}"
+      checksum_os_versions = bottle.send checksum_type
+      next unless checksum_os_versions
+      os_versions = checksum_os_versions.keys
+      os_versions.map! {|osx| MacOS::Version.from_symbol osx }
+      os_versions.sort.reverse.each do |os_version|
+        osx = os_version.to_sym
+        checksum = checksum_os_versions[osx]
+        puts "  #{checksum_type} '#{checksum}' => :#{osx}"
       end
     end
     puts "end"