God I would've loved to have seen this feud, this could've been one of the greatest feuds ever if it ever took place. All the promos, matches & segments the two would have done together would've been fantastic.
I can think of many time periods where this feud could've happened. There's 2001 obviously -- I made a thread recently about the 'Who Ran Over Stone Cold' storyline in 2000 and mentioned that I would like to have seen Raven revealed as the culprit, so he could come in as a main eventer right away, and had that happened, we could've seen some amazing feuds like Raven vs. Austin, Raven vs. Rock, Raven vs. HHH, Raven vs. Taker. Actually Raven vs. Taker would've been great for the Invasion storyline. Maybe he could've been the one revealed as the stalker of Taker's wife instead of DDP, that storyline is more up his alley than DDP's, it ruined DDP's image but would've played right in with Raven's. There was a recent thread that The Brain made about Jake Roberts, where he was supposed to join the WWF's creative team in 92, and I mentioned that if he had, we could've seen Scott Levy stay with the WWF since Roberts was his mentor & he would've benefited from him being on the team, and we could've possibly seen the Raven gimmick debut in the WWF instead of in ECW. I think if that happened, we might have seen Raven feud with Taker somewhere in like 96, and maybe they would've him paired him up with Goldust & Mankind as a deadly alliance to try & take out the Deadman. There's 1999, where he could've jumped to the WWF, if WCW allowed him to as part of his release. I've always thought if they allowed him to, Raven could've come in, feuded with Taker right away, he could've stolen away some of his Ministry members from him to form him own Flock, so we could get a Flock vs. Ministry feud, then at Summerslam, we see him & Taker compete in a feud ending Hell In A Cell match, where the winner would get all the Ministry members, and Raven wins with the help of the Ministry members -- who betray Taker -- and Raven & the Flock/Ministry kayfabe injure Taker in the Cell to write him off TV until he comes back in 2000, where he would get his revenge on Raven.
Any time this could've happened would've been a pleasure for me to watch. I think the only reason it didn't happen was because Raven wasn't Vince's creation and he was an ECW guy, and you know how Vince loved to bury the competition in order to make his product look strong. Such a shame that Vince has this mentality.