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Okay so @Death By Looch decided to track a few of these on his own... let's see what we've got. First, the WCW World Cup of Wrestling. It was a WCW vs. NJPW tournament that was decided by 7 singles matches. Looch's decision was to track the Cup from the first time one of the team members lost clean, so let's see...
Who holds the WCW World Cup of Wrestling?
[1995-12-27 Randy Savage]
1995-12-27 Ric Flair - beats "Macho Man" Randy Savage at WCW Starrcade. Looch had it as Chris Benoit being the first man to lose after the Cup had been won (to Steven Regal on the 1996-01-01 Nitro), but as it turns out, the first loss by a team member came during the event itself!
1996-01-22 Randy Savage (2) - beats Flair on WCW Monday Nitro
1996-02-11 Ric Flair (2) - beats Savage at WCW SuperBrawl VI
1996-04-22 The Giant - beats Flair on WCW Monday Nitro
[1996-07-01 Giant beats John Tenta and captures the UWF (Abrams) Southern States Title]
2024-04-07 Cody Rhodes - beats Roman Reigns at WWE WrestleMania 40
This was the same conclusion Looch came to, but his route was entirely different - it came through the 6th G1 Climax. (If you're wondering, Regal > Eddie Guerrero > Brian Pillman > Kevin Sullivan > Booty Man > Bam Bam Bigelow on the indies > Konnan > Ric Flair > Shinya Hashimoto > Riki Choshu.) Let's track that one, then!
Who holds the G1 Climax 6 trophy?
1996-08-06 Riki Choshu - beats Masahiro Chono at NJPW G1 Climax 6
[wait a minute, we've done this already! And Looch's message to me allows me to issue a CORRECTION! Harry Smith was previously listed as dropping the title this converges to - the UWF (Abrams) IC Title - to Andy Boy Simmonz on IPW:UK TV on 2006-09-22. But this listing has been removed from Cagematch, as it turns out this was just a rebroadcast of the match that happened on 2006-04-30! So the path changes completely. Again, shoutout to Looch for helping me notice this]
2006-08-12 Harry Smith - beats Morrison at a WWE live event
2007-04-12 Bradley Jay - beats Harry on DSW TV (dark)
2007-05-02 Nic Nemeth - beats Bradley on OVW TV (dark)
2007-06-06 Antoni Polaski - beats Nemeth on OVW TV
2007-06-22 Santino Marella - beats Polaski (aka Roadkill) at OVW Six Flags Summer Sizzler
2007-07-02 Umaga - beats Santino on WWE RAW
2007-07-28 Bobby Lashley - beats Umaga at a WWE live event
2007-07-30 Mr. Kennedy - beats Lashley on WWE RAW
2007-08-11 Umaga - beats Kennedy and Carlito at a WWE live event
[as it happens, Carlito brought Judy Bagwell, etc. into this match, so Umaga unifies that!]
2024-04-07 Cody Rhodes - beats Roman Reigns at WWE WrestleMania 40
Who holds the WCW World Cup of Wrestling?
[1995-12-27 Randy Savage]
1995-12-27 Ric Flair - beats "Macho Man" Randy Savage at WCW Starrcade. Looch had it as Chris Benoit being the first man to lose after the Cup had been won (to Steven Regal on the 1996-01-01 Nitro), but as it turns out, the first loss by a team member came during the event itself!
Who holds Johnny B. Badd's silly-looking mask and Maxx Payne's guitar?
1993-08-18 Johnny B. Badd - beats Payne in a Mask vs. Guitar match at WCW Clash of the Champions XXIV
1993-10-28 Lord Steven Regal - beats Badd at a WCW live event
1993-10-30 Dustin Rhodes - beats Regal at a WCW live event
[1993-11-04 Dustin claims the Coal Miner's Glove]
1994-05-01 Rick Rude - beats Sting at NJPW Wrestling Dontaku
Shame Man Mountain Rock never put his WWF-shaped guitar on the line. Why did they never do that?
2012-08-11 Caylee Turner - is released from WWE as the final champion
2012-11-01 ODB - beats Turner on TNA Impact Wrestling (dark)
2012-11-01 Jessie Godderz - beats ODB on TNA Impact Wrestling
2012-11-13 Eric Young - beats Godderz and Robbie E on TNA Impact Wrestling
2013-06-06 Austin Aries - beats Young on TNA Impact Wrestling
2013-06-29 Chris Sabin - beats Aries and Manik in a Three-Way match on TNA Impact Wrestling
[2013-07-18 Sabin beats Bully Ray...]
2016-11-13 Mike Gibson - beats Toxic and Mitch Thompson in a Three-Way Elimination match at BATTLEWAR 39
Caylee Turner is the sister of Alicia Fox. Very different fortunes, huh?
Btw... I dunno if you'd considered this yet, Sky, but what about some bad things people "win"? Those "If you lose the Match, then X" Matches?
I started one of those earlier with Col. Robert Parker losing to Flyin' Brian in a "Loser has to wear a Chicken Suit" Match, which immediately ended because Parker's next win was against a Jobber, who only had one Match...