diff --git a/Library/Homebrew/livecheck/strategy/pypi.rb b/Library/Homebrew/livecheck/strategy/pypi.rb
index 86f27df8a8..c598b33168 100644
--- a/Library/Homebrew/livecheck/strategy/pypi.rb
+++ b/Library/Homebrew/livecheck/strategy/pypi.rb
@@ -1,19 +1,21 @@
 # typed: strict
 # frozen_string_literal: true
 
+require "json"
+require "utils/curl"
+
 module Homebrew
   module Livecheck
     module Strategy
       # The {Pypi} strategy identifies versions of software at pypi.org by
-      # checking project pages for archive files.
+      # using the JSON API endpoint.
       #
-      # PyPI URLs have a standard format but the hexadecimal text between
-      # `/packages/` and the filename varies:
+      # PyPI URLs have a standard format:
       #
       # * `https://files.pythonhosted.org/packages/<hex>/<hex>/<long_hex>/example-1.2.3.tar.gz`
       #
-      # As such, the default regex only targets the filename at the end of the
-      # URL.
+      # This method uses the `info.version` field in the JSON response to
+      # determine the latest stable version.
       #
       # @api public
       class Pypi
@@ -44,10 +46,8 @@ module Homebrew
           URL_MATCH_REGEX.match?(url)
         end
 
-        # Extracts information from a provided URL and uses it to generate
-        # various input values used by the strategy to check for new versions.
-        # Some of these values act as defaults and can be overridden in a
-        # `livecheck` block.
+        # Extracts the package name from the provided URL and generates the
+        # PyPI JSON API endpoint.
         #
         # @param url [String] the URL used to generate values
         # @return [Hash]
@@ -58,40 +58,48 @@ module Homebrew
           match = File.basename(url).match(FILENAME_REGEX)
           return values if match.blank?
 
-          # It's not technically necessary to have the `#files` fragment at the
-          # end of the URL but it makes the debug output a bit more useful.
-          values[:url] = "https://pypi.org/project/#{T.must(match[:package_name]).gsub(/%20|_/, "-")}/#files"
-
-          # Use `\.t` instead of specific tarball extensions (e.g. .tar.gz)
-          suffix = T.must(match[:suffix]).sub(Strategy::TARBALL_EXTENSION_REGEX, ".t")
-          regex_suffix = Regexp.escape(suffix).gsub("\\-", "-")
-
-          # Example regex: `%r{href=.*?/packages.*?/example[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)\.t}i`
-          regex_name = Regexp.escape(T.must(match[:package_name])).gsub(/\\[_-]/, "[_-]")
-          values[:regex] =
-            %r{href=.*?/packages.*?/#{regex_name}[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)#{regex_suffix}}i
+          package_name = T.must(match[:package_name]).gsub(/[_-]/, "-")
+          values[:url] = "https://pypi.org/project/#{package_name}/#files"
+          values[:regex] = %r{href=.*?/packages.*?/#{package_name}[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)\.t}i
 
           values
         end
 
-        # Generates a URL and regex (if one isn't provided) and passes them
-        # to {PageMatch.find_versions} to identify versions in the content.
+        # Fetches the latest version of the package from the PyPI JSON API.
         #
         # @param url [String] the URL of the content to check
-        # @param regex [Regexp] a regex used for matching versions in content
+        # @param regex [Regexp] a regex used for matching versions in content (optional)
         # @return [Hash]
         sig {
           params(
-            url:    String,
-            regex:  T.nilable(Regexp),
-            unused: T.untyped,
-            block:  T.nilable(Proc),
+            url:     String,
+            regex:   T.nilable(Regexp),
+            _unused: T.untyped,
+            _block:  T.nilable(Proc),
           ).returns(T::Hash[Symbol, T.untyped])
         }
-        def self.find_versions(url:, regex: nil, **unused, &block)
-          generated = generate_input_values(url)
+        def self.find_versions(url:, regex: nil, **_unused, &_block)
+          match_data = { matches: {}, regex:, url: }
 
-          PageMatch.find_versions(url: generated[:url], regex: regex || generated[:regex], **unused, &block)
+          generated = generate_input_values(url)
+          return match_data if generated.blank?
+
+          match_data[:url] = generated[:url]
+
+          # Parse JSON and get the latest version
+          begin
+            response = Utils::Curl.curl_output(generated[:url])
+            data = JSON.parse(response.stdout, symbolize_names: true)
+            latest_version = data.dig(:info, :version)
+          rescue => e
+            puts "Error fetching version from PyPI: #{e.message}"
+            return {}
+          end
+
+          # Return the version if found
+          return {} if latest_version.blank?
+
+          { matches: { latest_version => Version.new(latest_version) } }
         end
       end
     end
diff --git a/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb b/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb
index 2cdd945c11..f42a3d174c 100644
--- a/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb
+++ b/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb
@@ -11,7 +11,7 @@ RSpec.describe Homebrew::Livecheck::Strategy::Pypi do
   let(:generated) do
     {
       url:   "https://pypi.org/project/example-package/#files",
-      regex: %r{href=.*?/packages.*?/example[_-]package[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)\.t}i,
+      regex: %r{href=.*?/packages.*?/example-package[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)\.t}i,
     }
   end