diff --git a/Library/Homebrew/bundle_version.rb b/Library/Homebrew/bundle_version.rb
index 12396ef0cc..4f2f017c97 100644
--- a/Library/Homebrew/bundle_version.rb
+++ b/Library/Homebrew/bundle_version.rb
@@ -62,8 +62,24 @@ module Homebrew
     end
 
     def <=>(other)
-      [version, short_version].map { |v| v&.yield_self(&Version.public_method(:new)) || Version::NULL } <=>
-        [other.version, other.short_version].map { |v| v&.yield_self(&Version.public_method(:new)) || Version::NULL }
+      return super unless instance_of?(other.class)
+
+      make_version = ->(v) { v ? Version.new(v) : Version::NULL }
+
+      version = self.version.then(&make_version)
+      other_version = other.version.then(&make_version)
+
+      difference = version <=> other_version
+
+      # If `version` is equal or cannot be compared, compare `short_version` instead.
+      if difference.nil? || difference.zero?
+        short_version = self.short_version.then(&make_version)
+        other_short_version = other.short_version.then(&make_version)
+
+        return short_version <=> other_short_version
+      end
+
+      difference
     end
 
     def ==(other)
diff --git a/Library/Homebrew/test/bundle_version_spec.rb b/Library/Homebrew/test/bundle_version_spec.rb
index 3ee120f913..7cec2e0bdf 100644
--- a/Library/Homebrew/test/bundle_version_spec.rb
+++ b/Library/Homebrew/test/bundle_version_spec.rb
@@ -3,6 +3,28 @@
 require "bundle_version"
 
 describe Homebrew::BundleVersion do
+  describe "#<=>" do
+    it "compares both the `short_version` and `version`" do
+      expect(described_class.new("1.2.3", "3000")).to be < described_class.new("1.2.3", "4000")
+      expect(described_class.new("1.2.3", "4000")).to be <= described_class.new("1.2.3", "4000")
+      expect(described_class.new("1.2.3", "4000")).to be >= described_class.new("1.2.3", "4000")
+      expect(described_class.new("1.2.4", "4000")).to be > described_class.new("1.2.3", "4000")
+    end
+
+    it "compares `version` first" do
+      expect(described_class.new("1.2.4", "3000")).to be < described_class.new("1.2.3", "4000")
+    end
+
+    it "does not fail when `short_version` or `version` is missing" do
+      expect(described_class.new("1.06", nil)).to be < described_class.new("1.12", "1.12")
+      expect(described_class.new("1.06", "471")).to be > described_class.new(nil, "311")
+      expect(described_class.new("1.2.3", nil)).to be < described_class.new("1.2.4", nil)
+      expect(described_class.new(nil, "1.2.3")).to be < described_class.new(nil, "1.2.4")
+      expect(described_class.new("1.2.3", nil)).to be < described_class.new(nil, "1.2.3")
+      expect(described_class.new(nil, "1.2.3")).to be > described_class.new("1.2.3", nil)
+    end
+  end
+
   describe "#nice_version" do
     expected_mappings = {
       ["1.2", nil]            => "1.2",
@@ -25,10 +47,4 @@ describe Homebrew::BundleVersion do
       end
     end
   end
-
-  describe "#<=>" do
-    it "does not fail when a `version` is nil" do
-      expect(described_class.new("1.06", nil)).to be < described_class.new("1.12", "1.12")
-    end
-  end
 end