diff --git a/Library/Homebrew/cleanup.rb b/Library/Homebrew/cleanup.rb
index 00ca1e00d0..68b22eb204 100644
--- a/Library/Homebrew/cleanup.rb
+++ b/Library/Homebrew/cleanup.rb
@@ -101,6 +101,15 @@ module Homebrew
         package.tap_git_head != git_head
       end
 
+      sig { params(formula: Formula).returns(T::Set[String]) }
+      def excluded_versions_from_cleanup(formula)
+        @excluded_versions_from_cleanup ||= {}
+        @excluded_versions_from_cleanup[formula.name] ||= begin
+          eligible_kegs_for_cleanup = formula.eligible_kegs_for_cleanup(quiet: true)
+          Set.new((formula.installed_kegs - eligible_kegs_for_cleanup).map { |keg| keg.version.to_s })
+        end
+      end
+
       sig { params(pathname: Pathname, scrub: T::Boolean).returns(T::Boolean) }
       def stale_formula?(pathname, scrub)
         return false unless HOMEBREW_CELLAR.directory?
@@ -131,6 +140,7 @@ module Homebrew
           nil
         end
 
+        formula_excluded_versions_from_cleanup = nil
         if formula.blank? && formula_name.delete_suffix!("_bottle_manifest")
           formula = begin
             Formulary.from_rack(HOMEBREW_CELLAR/formula_name)
@@ -140,6 +150,9 @@ module Homebrew
 
           return false if formula.blank?
 
+          formula_excluded_versions_from_cleanup = excluded_versions_from_cleanup(formula)
+          return false if formula_excluded_versions_from_cleanup.include?(version.to_s)
+
           # We can't determine an installed rebuild and parsing manifest version cannot be reliably done.
           return false unless formula.latest_version_installed?
 
@@ -158,6 +171,9 @@ module Homebrew
           return true unless patch_hashes&.include?(Checksum.new(version.to_s))
         elsif resource_name && stable && (resource_version = stable.resources[resource_name]&.version)
           return true if resource_version != version
+        elsif (formula_excluded_versions_from_cleanup ||= excluded_versions_from_cleanup(formula).presence) &&
+              formula_excluded_versions_from_cleanup.include?(version.to_s)
+          return false
         elsif (formula.latest_version_installed? && formula.pkg_version.to_s != version) ||
               formula.pkg_version.to_s > version
           return true
diff --git a/Library/Homebrew/test/cleanup_spec.rb b/Library/Homebrew/test/cleanup_spec.rb
index e622a1d8be..ab97061c8d 100644
--- a/Library/Homebrew/test/cleanup_spec.rb
+++ b/Library/Homebrew/test/cleanup_spec.rb
@@ -417,6 +417,8 @@ RSpec.describe Homebrew::Cleanup do
         FileUtils.touch testball
         FileUtils.touch testball_resource
         (HOMEBREW_CELLAR/"testball"/"0.0.1").mkpath
+        # Create the latest version of testball so the older version is eligible for cleanup.
+        (HOMEBREW_CELLAR/"testball"/"0.1/bin").mkpath
         FileUtils.touch(CoreTap.instance.new_formula_path("testball"))
       end