In Star Fox 64, Star Wolf makes very little mention of Jame Mcloud.
But may very well have run into him in the past.

one reason being how old Wolf is. He's about, I'd say 27 some years old?
He may have been a teenager when he met James Mcloud.

I would also like to ask the question, what happened recently between
Star Fox and Star Wolf in Star Fox 64? I don't think that Fox met
Wolf on Fincha, Fox says the following: "Great, Star Wolf, just what I need to see"
I makes it sound like he's met Wolf before. At the very least he's heard of him.

Also, if you fail the mission at Finch (Fourtuna) and Falco doesn't need to go
in for repairs, Falco will say the following:

"So that's Star Wolf"

Apparently he's heard about the mercenary before, but has never
actually seen him. Has Fox told Falco about Wolf in the past? From
his own experience even?

Sword legion : I think I may be able to take a crack at this. Now with the connection, speculation would have you right. It is believed when James McCloud was still around Star Wolf was a Teen at best. Some say he was trying to follow in James' steps as an ar-wing pilot, a student-master type deal which eventually turned into a rivalry between Wolf and James. But still something left open for determination but apparently some comics of Star Fox involving Wolf and his past has some kind of evidence to this.

As for the rivalry between Fox and Wolf, it is a possibility that Fox heard of Wolf from his father and from some of Wolf's illegal acts before Andross started the war or maybe even met Wolf during the rivalry phaze. I would say because Fox is James' son and takes over the Star Fox team that it was inevitable to want to hold this rivalry to Fox since James dies. Since Star Wolf was hired by Andross it may be a possibility they had a big hand in James' death since the team members of Star Wolf make remarks to this especially Wolf's line "You'll be joining your dad soon, Fox!" The reason I say they probably had a hand in it is because the opening of Star Fox 64 mentions Pigma leading Peppy and James into a trap. The rest of the Star Wolf team could have been waiting on Venom since they were hired by Andross. Plus I don't believe James and Andross had some rivalry, at least to my extent so that leaves Star Wolf to be the cause of death for James. With that, Andross was probably paying Wolf to make sure James' son didn't succeed where his Father failed seeing as how a lot of keypoints have Wolf showing up before Fox can complete specific missions.

As for Falco and Star Wolf there are some sources (typically old mangas based on Star Fox and one of Falco himself) pointing that Falco has had a Rivalry with Leon Powalski that dates back before Falco ever joined Star Fox. With that being said Falco probably heard of Leon joining Star Wolf and heard of what they've done but never had confrontation until the Lylat Wars. It is a possibility that Falco also heard of Star Wolf from Fox.

So there's that. Read it and tell me if that helps at all. I can always dig around for some more answers.

zerothesaint :

Wow, I only looked into it a little.
You really answered my question and made a good post. 

Thanks man.

I would really have to agree with the idea of Wolf and his team 
waiting for James Mcloud on Venom when Pigma set them up.

Sword legion : Next to Mega Man, Star Fox places as my second most favorite game series ever.  I tend to do a lot of research on plots and such with games that I love, after I beat them of course for the sake of spoilers. But hey, I like to enlighten others on what I know or strive to give that answer to those who seek specific things.

If I could find direct sources not just for verification but just for the sake of fun I so totally would. I have to say though, with what the Star Fox series leaves out during he game makes for good questions and speculations by the fans which just makes everything all the more fun to see what others think or believe. And that is why fandom can be an amazing thing!