| This answer is opinion-based.|
Due to lack of canonical information in the franchise, there is no definite answer to this question.
Possibly, though perhaps only by close luck. Both are illustrated to be equally strong and skilled, as seen in their fight in the Spirit Realm as well as their fight in the mortal realm, which Oogway describes "shook the earth" and "finally" came to an end. In addition, Oogway had been seriously wounded in a battle, but Kai had not, although the specific circumstances of the battle are unknown.