We all know naruto surpassed kakashi after defeating kakuzu and later after mastering sage mode but could it be that hebi sasuke had already surpassed kakashi before naruto? i am talking about the sasuke who fought itachi(shippuden)
Well... While Kakashi did claim that Naruto surpassed him after his fight with Kakuzu, I'd say he didn't really surpass Kakashi until he got SM. And Sasuke surpassed Kakashi when he got MS, but definitely not before that.
So... If I remember correctly Naruto got SM before Sasuke got MS right??? Or was it the other way around...
In any case whomever got that particular power up first, surpassed Kakashi first.