Should reggie really have won
Ash was up against his butterfree, knowing he had a Charmander, Ash should have saved his Squirtle for that. His Pigeotto had an advantage anyway, second was the charmander, he could have still had his Squirtle, or why not use Kingler? Third the Pikachu, maybe a face off between Reggies ansd his own? or play it safe and use bulbasaur.
If you could fight Reggie in Gold, I would have used a Tyranitor ands got all three of them, but Ash didn't have one of them.