What about best & worst match of the year on the same show? Which surely will happen this year for Summerslam.
Great question. Let's look at the WON Awards archives.
YES, in 1987.
Match of the year was Ricky Steamboat versus Randy Savage at WrestleMania III. Worst match of the year was Andre the Giant versus Hulk Hogan at WrestleMania III.
As far as I can tell since then no single show has had a match was ranked both MOTY and worst match of the year. However, it's been very close at least three times in the past decade.
Exhibit One: Royal Rumble 2003
5. Scott Steiner defeated Triple H (c) (with Ric Flair) by disqualification (Singles match for the World Heavyweight Championship) 18:14
6. Kurt Angle (c) (with Shelton Benjamin and Charlie Haas) defeated Chris Benoit (Singles match for the WWE Championship) 19:50
It's remarkable that these two matches went back-to-back with similar stips (top titles) and similar length (18-20 minutes).
Angle/Benoit was #2 for MOTY (behind Misawa/Kobashi 3/1/03 Tokyo). Meanwhile, HHH/Steiner won worst match of the year.
Exhibit Two: WrestleMania XXV (4/5/2009)
7. The Undertaker defeated Shawn Michaels (Singles match) 30:41
9. Triple H (c) defeated Randy Orton (Singles match for the WWE Championship)
Taker/Shawn won match of the year (second place was Davey Richards/Shingo Takagi 9/6/09). Meanwhile, HHH/Orton got second place for worst match of the year. However, that year's worst match winner has gone down in history for it's terribleness: TNA's Sharmell VS. Jenna Morasca 7/19/09.
Exhibit Three: WrestleMania XXVI (3/28/2010)
7. Bret Hart defeated Mr. McMahon by submission (No Holds Barred Lumberjack match with Bruce Hart as the special guest referee) 11:09
11. The Undertaker defeated Shawn Michaels (No Disqualification Streak vs. Career match) 23:59
Taker/Shawn repeated MOTY honors with HBK's retirement match. (Second place was Tyler Black vs. Davey Richards 6/19/10)
Meanwhile, the Bret Hart/McMahon was a head-scratching and awful affair. Still, it was only the second worst match of the year in the eye's of voters. Kaitlyn vs Maxine from NXT 10/19/10 was that year's worst offense. I feel that in time people won't remember that terrible NXT match but the stain of McMahon/Hart will stick around in people's minds.
Trivia Note: Clash of the Champions I vs WWF WrestleMania IV on 3/27/88
Clash of the Champions went #1/#2 in the MOTY balloting (Flair/Sting won followed by Midnight Express/Fantastics) in Greensboro.
Meanwhile, up in Atlantic City, WMIV had Warrior/Hercules (finished second for Worst Match of the Year) and Jake Roberts/Rick Rude (finished fifth for Worst Match of the Year).
Wonder what atrocity won worst match of the year in 1988? All Japan's (Great) Hiroshi Wajima vs (Megaman) Tom McGee (4/21/88).