Basically I want to look at this thread beyond just the financial or ratings standpoint, but also in a qualitative sense in hindsight.
I'll mostly be referencing PPVs since that is mostly what's on the network.
1991-I have to go with the WWF. I don't really see a big draw in what WCW was doing during this year and they were starting alienate Flair. Luger vs Ron Simmons just isn't a draw to me. Hogan had taken the forefront of the company again the WWF were cashing in on the Desert Storm conflict by pitting Hogan against Slaughter, and the Warrior and Hogan versus Sgt. Slaughter, General Adnan and Col. Mustafa.
1992-WWF. Sting vs. Luger earlier in that year was a draw, but most of the PPV headliners were watered down. Sting is the about the only big talent with the company until Vader comes along at the end of the year. In the WWF Flair had jumped ship, won the Rumble and had a great match with Savage despite missing a huge opportunity for WWF to put something together with him and Hogan. Hogan is back (but I believe among the roid scandal), and wrestles with Sid Vicious in a yawner at Wrestlemania where Papa Shango comes out for some reason but is countered by the Warrior. Hart begins his first title reign after beating Flair, but is premature. Savage and Warrior try to recreate a Mega Powers team against Flair and Ramon which is decent.
1993-Close, but I have to go with WCW. For WCW this is the year of Vader as he is at the forefront of the story lines and an impressive gimmick. Bulldog is decent, and WCW gets Flair back toward the end of the year to wrestle against Vader at the height of Vader's dominance. Rude and Flair have a good match at Fall Brawl. For the WWF, I think things start to decline and there isn't a clear cut formula for success at this point. Your Wrestlemania is another Hogan debacle where he is in a match but refuses to become a tag champion because it's beneath him, and then pulls the goofy ending after Yokozuna beats Bret. Yokozuna ends up with the title and a lengthy run with small marketability. WWF tries to recreate Hogan with Luger, but it simply doesn't work.
1994-WCW, they had the bigger names at this point. Vader, Flair, Sting, and Hogan were all on the roster at this point and rotating through the main events all year. Hogan manages to ruin a Starrcade by putting the barber in a match against him. WWF seems to only have Bret and The Undertaker at this point. Yokozuna is involved heavily throughout the year but there's only so much of a fat guy that you can't pick up that's entertaining. WWF has a strong midcard with guys like Bulldog, Owen, Michaels, Ramon, and Diesel.
In regards to the Monday Night Wars:
1995-While close, I would say WCW was winning this year. Despite running the goofy Dungeon of Doom angle, WCW was loaded with superstars like Flair, Hogan, Savage, Luger, the newly emerged Giant, and Vader early on in the year. I believe the midcard was stronger for WCW at the time as well as the WWF was heavily cartoonish. The main event scene for the WWF was not bad, I just don't think Diesel panned out to be the huge draw despite headlining so many PPVs that year. WWF ruined their biggest match of the year having Bam Bam Bigelow go up against LT at WM.
1996-Obviously the WCW pulled ahead with the NWO angle about midway through the year. Hart and Michaels were great talents, but the story lines and heat just weren't there for WWF to be competitive. Michaels proves to be inconsistent.
1997-WCW. The NWO is in full swing for the WCW. While the main event scene still revolved around familiar faces, they weren't quite to the point of being stale and tired yet. Sting vs. Hogan is the most anticipated match of all time despite being botched. The WCW mid card was very exciting despite having little heat. WWF is flirting with the Attitude era at this point, the Canada vs. America angle is very interesting, but not going to win it for them. Austin's push is put on ice due to a neck injury, but the grittier product is starting to emerge in WWF and they are starting to pull themselves out of the slump despite losing Hart at the end of the year.
1998-Best year to be a wrestling fan. WWF is back out of the gutter and running strong against WCW. The Attitude era is in full swing and the NWO doesn't seem quite as entertaining so they form two different factions in an attempt to be fresh. The Warrior is brought on board late that year, and misused. Goldberg's very popular. The year of Austin is at hand and very interesting angles pan out. WWF produces a very gritty product, despite not having the midcard talent that the WCW has, the WWF wins out because of a much better main event scene.
1999-Finger Poke of Doom and reformation of the WCW puts the brakes on WCW. WWF wins this year decidedly as WCW doesn't seem to want to recover.
2000-WWF. WCW is not doing anything special at this point.
I'll mostly be referencing PPVs since that is mostly what's on the network.
1991-I have to go with the WWF. I don't really see a big draw in what WCW was doing during this year and they were starting alienate Flair. Luger vs Ron Simmons just isn't a draw to me. Hogan had taken the forefront of the company again the WWF were cashing in on the Desert Storm conflict by pitting Hogan against Slaughter, and the Warrior and Hogan versus Sgt. Slaughter, General Adnan and Col. Mustafa.
1992-WWF. Sting vs. Luger earlier in that year was a draw, but most of the PPV headliners were watered down. Sting is the about the only big talent with the company until Vader comes along at the end of the year. In the WWF Flair had jumped ship, won the Rumble and had a great match with Savage despite missing a huge opportunity for WWF to put something together with him and Hogan. Hogan is back (but I believe among the roid scandal), and wrestles with Sid Vicious in a yawner at Wrestlemania where Papa Shango comes out for some reason but is countered by the Warrior. Hart begins his first title reign after beating Flair, but is premature. Savage and Warrior try to recreate a Mega Powers team against Flair and Ramon which is decent.
1993-Close, but I have to go with WCW. For WCW this is the year of Vader as he is at the forefront of the story lines and an impressive gimmick. Bulldog is decent, and WCW gets Flair back toward the end of the year to wrestle against Vader at the height of Vader's dominance. Rude and Flair have a good match at Fall Brawl. For the WWF, I think things start to decline and there isn't a clear cut formula for success at this point. Your Wrestlemania is another Hogan debacle where he is in a match but refuses to become a tag champion because it's beneath him, and then pulls the goofy ending after Yokozuna beats Bret. Yokozuna ends up with the title and a lengthy run with small marketability. WWF tries to recreate Hogan with Luger, but it simply doesn't work.
1994-WCW, they had the bigger names at this point. Vader, Flair, Sting, and Hogan were all on the roster at this point and rotating through the main events all year. Hogan manages to ruin a Starrcade by putting the barber in a match against him. WWF seems to only have Bret and The Undertaker at this point. Yokozuna is involved heavily throughout the year but there's only so much of a fat guy that you can't pick up that's entertaining. WWF has a strong midcard with guys like Bulldog, Owen, Michaels, Ramon, and Diesel.
In regards to the Monday Night Wars:
1995-While close, I would say WCW was winning this year. Despite running the goofy Dungeon of Doom angle, WCW was loaded with superstars like Flair, Hogan, Savage, Luger, the newly emerged Giant, and Vader early on in the year. I believe the midcard was stronger for WCW at the time as well as the WWF was heavily cartoonish. The main event scene for the WWF was not bad, I just don't think Diesel panned out to be the huge draw despite headlining so many PPVs that year. WWF ruined their biggest match of the year having Bam Bam Bigelow go up against LT at WM.
1996-Obviously the WCW pulled ahead with the NWO angle about midway through the year. Hart and Michaels were great talents, but the story lines and heat just weren't there for WWF to be competitive. Michaels proves to be inconsistent.
1997-WCW. The NWO is in full swing for the WCW. While the main event scene still revolved around familiar faces, they weren't quite to the point of being stale and tired yet. Sting vs. Hogan is the most anticipated match of all time despite being botched. The WCW mid card was very exciting despite having little heat. WWF is flirting with the Attitude era at this point, the Canada vs. America angle is very interesting, but not going to win it for them. Austin's push is put on ice due to a neck injury, but the grittier product is starting to emerge in WWF and they are starting to pull themselves out of the slump despite losing Hart at the end of the year.
1998-Best year to be a wrestling fan. WWF is back out of the gutter and running strong against WCW. The Attitude era is in full swing and the NWO doesn't seem quite as entertaining so they form two different factions in an attempt to be fresh. The Warrior is brought on board late that year, and misused. Goldberg's very popular. The year of Austin is at hand and very interesting angles pan out. WWF produces a very gritty product, despite not having the midcard talent that the WCW has, the WWF wins out because of a much better main event scene.
1999-Finger Poke of Doom and reformation of the WCW puts the brakes on WCW. WWF wins this year decidedly as WCW doesn't seem to want to recover.
2000-WWF. WCW is not doing anything special at this point.