diff --git a/python/lib/dependabot/python/requirement.rb b/python/lib/dependabot/python/requirement.rb
index 62fc86da1cf..62414a29114 100644
--- a/python/lib/dependabot/python/requirement.rb
+++ b/python/lib/dependabot/python/requirement.rb
@@ -87,7 +87,7 @@ def convert_python_constraint_to_ruby_constraint(req_string)
         return nil if req_string == "*"
 
         req_string = req_string.gsub("~=", "~>")
-        req_string = req_string.gsub(/(?<=\d)[<=>].*/, "")
+        req_string = req_string.gsub(/(?<=\d)[<=>].*\Z/, "")
 
         if req_string.match?(/~[^>]/) then convert_tilde_req(req_string)
         elsif req_string.start_with?("^") then convert_caret_req(req_string)
diff --git a/python/spec/dependabot/python/requirement_spec.rb b/python/spec/dependabot/python/requirement_spec.rb
index 789945206e2..001a2731039 100644
--- a/python/spec/dependabot/python/requirement_spec.rb
+++ b/python/spec/dependabot/python/requirement_spec.rb
@@ -116,6 +116,17 @@
       end
     end
 
+    context "with multiple operators after the first" do
+      let(:requirement_string) { ">=2.0<2.1<2.2" }
+      # Python ignores operators after the first!
+      it { is_expected.to eq(Gem::Requirement.new(">=2.0")) }
+
+      context "separated with a comma" do
+        let(:requirement_string) { ">=2.0,<2.1,<2.2" }
+        it { is_expected.to eq(Gem::Requirement.new(">=2.0", "<2.1", "<2.2")) }
+      end
+    end
+
     context "with an array" do
       let(:requirement_string) { ["== 1.3.*", ">= 1.3.1"] }
       its(:to_s) do