I think it's possible Team Gai was, but Lee's future isn't in jeopardy now too so there will be much to be happy about for everyone. 

We can decide it in the roleplay itself since Sakura is the one who's meant to benefit from Kakashi the most! So she can decide if she'd like to stop and train and get to town later in the evening or get to town sooner and proceed further before they train for the rest of the evening. She's restless so she may want to do it now before or a little after lunch. I think maybe it should just be a small Lee v.s. Sakura thing, but only at Sakura's insistence. Kakashi wouldn't want her to do it yet, he'd express that she's not quite ready for Lee yet, and Sakura can be bothered by this and challenge Lee. Lee's just so far ahead of her that it'll be a stomp at this point, and that might wound Sakura's pride a little. A lot of ways to deal with this, but Kakashi v.s. Gai can't really occur, no time for a contest at that level.