For the record, I actually voted for Benoit, and I credit JMT with convincing me to do so in a prior post. But I read this and thought I'd jump in just to make sure credit is given where it is due.
Finally, a challenge. Also, its nice to see D-Man has hacked into Irish's account.
Don't worry, if someone attacked my Wife - I'd come to her aid too. Its nice to see you sticking up for your lover, IC.
I'll assume you disqualify the Ironman Match because you think of the overtime as "controversy." Despite the fact that Hart's kayfabe assertion that he didn't prepare for a one hour match PLUS overtime is inherently flawed, since I don't see how you'd prepare differently for a 62 minute match as you would a 60-minute match.
Well, considering the entire build-up to this contest was a 60-minute Iron Man match. Not a 60(plus) minute Iron Man match, I'd say you have to include the controversy of them re-starting the match when Bret Hart clearly had Shawn Michaels moments away from tapping out/submitting.
If the match would've just continued beyond the end of the 60 minutes, like it should have if they ever had any intention on continuing.. Shawn Michaels would have and should have lost to the Sharpshooter.
On this note, since you brought up the Iron Man match and I figured someone would try replying with this as a "clean" victory.. it took HBK over 1 hour to defeat Bret Hart. Benoit has fought Hart, and won, in less time. (granted, for argument sake he's also lost just as many times as HBK has, to Hart as well.)
1. SummerSlam 1995 - vs Razor Ramon: This was the Wrestlemania 10 rematch, another ladder match that saw IC Champ Shawn Michaels this time victorious over Razor Ramon in a 25-minute ladder match. The neat part of this match, as opposed to the WMX match, was that the ladder could not be used as a weapon. Shawn was the more creative and more prepared of the two men, and won the match, retaining the IC Title. A ladder match at SummerSlam is pretty significant, especially when you consider that the Michaels / Ramon match had to buoy the "main event" of Diesel vs Mabel.
Okay, before I completely dismiss this because in D-Man's own words.. the Shawn Michaels he was referring to was the 1996-1998 version. Not the midcard version. So, if you somehow can make me believe this match re-happened in the timeline your boyfriend set up then sure, I'll count it.
Anyways, with that being said what the shit were you smoking?
"The neat part of this match, as opposed to the WMX match, was the ladder could not be used as a weapon." (yeah, you actually said that)
So, I'm assuming you missed 40-60% of this match, where Razor kept using the ladder to injure Shawn's knee. Or where Shawn used the ladder to injure Razor's back/stomach.
Also, I love how you think the gimmick match had to fight
so hard to compete against two guys who couldn't have been even more uncompatable with each other. No one took Mabel as a credible contender to the Heavyweight title, and that match lasted all of 10 minutes. Benoit's victory over Orlando Jordan in 24 seconds at Summerslam could have competed and out-shined that shit-fest. (of course, for purpose sake this last paragraph was in relation to you claiming the ladder match had to try and out-do the Main Event of that year's Summerslam.)
I will also assume that since winning the Royal Rumble, despite being a massive accomplishment, isn't a "title match" and thus you wouldn't count it. So consider this a footnote - Michaels won back to back Rumbles, '95 and '96.
Sure, let's toss this in. Again, its not exactly falling within the realm of what D-Man himself set-up as the correct timeline.. but I'm game to prove why its pointless.
Shawn Michaels won the 1995 Rumble entering at #1. An impressive victory, one I would greatly consider amazing. But that wasn't the year we were discussing, so unless we will go on to talk of Shawn's failure at WMXI then we'll jump to the 1996 Rumble..
At which point, HBK entered #19 and did a massive overhaul of the ring. Eliminating Vader and Yokozuna at the same time. (Granted, they had one another half way over and momentum carried them while Shawn got credit, but sure, we'll let Shawn shine here) Continuing onward.. in the final moments of the Rumble, it was HBK Superkicking his best friend in the face, technically from behind (Diesel had only a mere second to turn around only to see a foot planted upside his head) to gain the elimination and victory.
On the flip side of this; Chris Benoit started at #1 in 2004.. and in the final moments of his Royal Rumble, he was one-on-one against the massive Big Show. An individual that typically takes a handful or more of Superstars to eliminate.. yet Benoit did it by himself, straight forward, with a headlock/choke.
Whats this tell you? To me, it says this..
Shawn Michaels wasn't viewed as credible enough to the company to allow him the opportunity to go one-on-one with anyone before giving him the final elimination. He had to do it suddenly, from behind. Whereas Chris Benoit fought all the way from the #1 spot (for almost double the amount of time HBK did in 1995, mind you) and won by eliminating not just the final individual in a one-on-one situation.. but an individual much larger, stronger, and overall arguably better than Diesel was in the Big Show.
So, how is HBK's Rumble victory to be viewed as better than Benoit's? I mean, thats all we can discuss here since again D-Man didn't define the timeline to allow this as what he was jabbering about in his "Championship timetable."
2. In Your House 7 - Good Friends, Better Enemies: Michaels, not known for being a brawler, defeated Diesel, who was in fact known for being a brawler, in a no holds barred Main Event. That win enabled Shawn to retain the WWF Title.
Kevin Nash was leaving the Company. In the Main Event of Wrestlemania XI, Diesel destroyed Shawn Michaels. A match that had rules, I might add - just like the Iron Man match, here.
In the Midcard Pay per view that was considered In Your House, Shawn Michaels used a variety of weapons to dispatch a man who was leaving the Company.
Yes, what a credible victory that was.

I'm sure Shawn had more than a handful of House Show victories under his belt as well. Would you like to use those as well???
3. King of the Ring 1996 - vs British Bulldog: There was special guest referee Mr. Perfect, and the only interference was Owen Hart's on Bulldog's behalf. Shawn won the match with the Super Kick. Bulldog was billed as a serious contender to BOTH Michaels and Hart during the mid-90's, and deservedly so.
The King of the Ring match ended as cleanly as anything Shawn Michaels had done that Year, I'll give you that. But the controversy in relation to this is that it took Shawn Michaels two months before he could properly prove he could defeat the mid-card level, Main Event raised, British Bulldog.
A month prior to this, the Bulldog had pinned Shawn's shoulders to the mat, cleanly in the ring. Yet he wasn't awarded the Heavyweight title - nor was the title held up. The match was viewed as a double pinfall, yet the Champion retained. (however, at Wrestlemania when the match went to a draw, they allowed the contest to continue even though the challenger likely would have been moments away from repeating his Survivor Series 1992 finale.)
Also, though not a title match, you cannot throw out the fact that Shawn put on a classic match against the Undertaker in the first ever Hell in a Cell match, which Michaels won. Yes, Kane debuted, but you cannot just throw out the brutality nor the importance of that match.
Well, when you can explain to me when, where and how interference is going to happen here and help Shawn Michaels gain a victory he otherwise would've never had. I'll give you the HBK nod. Until then, I find that all you're doing here is burying HBK worse, in technically claiming that the only way he can win matches viewed in a Main stream importance is by the outside interference of others.
For purpose sake, because I'm on a roll at this point.. Shawn Michaels never even once.. not ONCE.. had the Undertaker "in the red" throughout this match. He hit Sweet Chin Music, and the Undertaker sat up in a heartbeat.
Shawn Michaels was beaten, bloodied and broken by the time this contest was over. The Tombstone laid HBK out, and it was all over but the three count - which couldn't happen, because Kane decided to screw with his brother's head.
Are we stopping at 1998, or can we keep going? Because I can bring up the Elimination Chamber win over HHH if you'd like...
Another situation that falls just short of your lover's timeline that he claimed
this version of HBK would be fighting.
However, if you consider the version of Shawn Michaels competing in this contest the same Shawn Michaels that won the title in 2002.. then surely you'd allow me to run down all the numerous losses he's gained over that same time, to names vastly less than superior to Chris Benoit.
Are we done here? Have I proven my point, or do I need to continue in showing you both how wrong I believe you are? Because if I need to continue, you're gonna have to do much better than this.