diff --git a/lib/openapi_first/router.rb b/lib/openapi_first/router.rb
index 9f04ec8a..5f7189fc 100644
--- a/lib/openapi_first/router.rb
+++ b/lib/openapi_first/router.rb
@@ -97,10 +97,15 @@ def find_path_item(request_path)
       found = @static[request_path]
       return [found, {}] if found
 
-      @dynamic.find do |_path, path_item|
+      matches = @dynamic.filter_map do |_path, path_item|
         params = path_item[:template].match(request_path)
-        return [path_item, params] if params
+        next unless params
+
+        [path_item, params]
       end
+      return matches.first if matches.length == 1
+
+      matches&.min_by { |match| match[1].values.sum(&:length) }
     end
   end
 end
diff --git a/spec/router_spec.rb b/spec/router_spec.rb
index 4ebd5c4f..6546d121 100644
--- a/spec/router_spec.rb
+++ b/spec/router_spec.rb
@@ -8,7 +8,8 @@
       [
         double(path: '/{id}', request_method: 'get'),
         double(path: '/{id}', request_method: 'patch'),
-        double(path: '/a', request_method: 'get')
+        double(path: '/a', request_method: 'get'),
+        double(path: '/a{format}', request_method: 'get')
       ]
     end
 
@@ -30,6 +31,12 @@
       expect(router.match('GET', '/c/d').error).to have_attributes(type: :not_found)
     end
 
+    it 'can match a path fragment with a variable' do
+      match = router.match('GET', '/a.json')
+      expect(match.request_definition.path).to eq('/a{format}')
+      expect(match.request_definition).to be(requests[3])
+    end
+
     it 'returns an incomplete match for unknown request method' do
       expect(router.match('DELETE', '/b').error).to have_attributes(type: :method_not_allowed)
     end