sources: http://www.thehistoryofwwe.com/08.1.htm and http://www.thehistoryofwwe.com/08.2.htm

(More than 150 matches
CM Punk: 169 matches (115-50-3 and 1 other match) = 70% win
Kane: 157 matches (82-70-2 and 3 other matches) = 54% win

More than 125 matches
John Morrison: 143 matches (81-56-5 and 1 other match) = 59% win
Cody Rhodes: 142 matches (96-44-2) = 69% win
Kofi Kingston: 139 matches (100-39-0) = 72% win
MVP: 139 matches (18-116-3 and 2 other matches) = 13% win
Shelton Benjamin: 139 matches (64-74-1) = 46% win
Triple H: 137 matches (118-15-4) = 89% win
Batista: 136 matches (86-40-8 and 2 other matches) = 68% win
Chris Jericho: 136 matches (62-68-6) = 48% win
Jeff Hardy: 136 matches (90-42-3 and 1 other match) = 68% win
Finlay: 135 matches (96-33-4 and 2 other matches) = 74% win
Matt Hardy: 135 matches (101-29-3 and 2 other matches) = 78% win
Mike Mizanin: 133 matches (77-50-4 and 2 other matches) = 61% win
Mark Henry: 132 matches (51-77-3 and 1 other match) = 40% win
Beth Phoenix: 129 matches (69-59-0 and 1 other match) = 54% win

More than 100 matches
Chavo Guerrero Jr.: 123 matches (30-91-1 and 1 other match) = 25% win
Mickie James: 119 matches (74-43-1 and 1 other match) = 63% win
Santino Marella: 113 matches (42-69-2) = 38% win
Brian Kendrick: 112 matches (51-60-1) = 46% win
Carlito Caribbean Cool: 107 matches (53-53-1) = 50% win
Edge: 103 matches (34-68-1) = 33% win
Snitsky: 102 matches (40-57-2 and 3 other matches) = 41% win
John Bradshaw Layfield: 100 matches (28-68-3 and 1 other match) = 29% win

More than 75 matches
the Big Show: 100 matches (55-40-3 and 2 other matches) = 58% win
Michelle McCool: 97 matches (72-23-1 and 1 other match) = 76% win
Jamie Noble: 96 matches (43-52-1) = 45% win
the Undertaker: 95 matches (84-7-4) = 92% win
Charlie Haas: 91 matches (20-69-2) = 22% win
the Great Khali: 90 matches (45-38-5 and 2 other matches) = 54% win
Vladimir Kozlov: 86 matches (49-34-3) = 59% win
John Cena: 85 matches (65-16-3 and 1 other match) = 80% win
Randy Orton: 81 matches (31-46-4) = 40% win
Shawn Michaels: 81 matches (63-14-3 and 1 other match) = 82% win
Lance Cade: 78 matches (28-49-1) = 36% win
Tommy Dreamer: 77 matches (29-45-2 and 1 other match) = 39% win

More than 50 matches
William Regal: 75 matches (31-42-1 and 1 other match) = 42% win
Kelly Kelly: 73 matches (53-14-0 and 6 other matches) = 79% win
Natalya Neidhart: 73 matches (23-46-1 and 3 other matches) = 33% win
Rey Mysterio Jr.: 72 matches (55-17-0) = 76% win
Ted Dibiase Jr.: 72 matches (46-25-1) = 65% win
Zach Ryder: 72 matches (21-50-1) = 30% win
Maryse: 71 matches (16-48-0 and 7 other matches) = 25% win
Curt Hawkins: 70 matches (21-48-1) = 30% win
Shad Gaspard: 70 matches (30-38-2) = 44% win
JTG: 68 matches (28-38-2) = 42% win
Victoria: 68 matches (14-46-1 and 7 other matches) = 23% win
Bob Holly: 67 matches (53-13-1) = 80% win
Festus: 67 matches (27-38-2) = 42% win
Umaga: 67 matches (17-47-2 and 1 other match) = 27% win
Ron Killings: 66 matches (34-32-0) = 52% win
Super Crazy: 64 matches (27-36-1) = 43% win
Trevor Murdoch: 64 matches (8-55-1) = 13% win
Maria: 63 matches (43-19-0 and 1 other match) = 69% win
Jimmy Wang Yang: 59 matches (12-46-1) = 21% win
Jesse: 58 matches (23-34-1) = 40% win
Paul Birchill: 58 matches (28-29-1) = 49% win
D-Lo Brown: 55 matches (21-34-0) = 38% win
Mike Knox: 55 matches (18-37-0) = 33% win
Ken Kennedy: 52 matches (25-26-0 and 1 other match) = 49% win

More than 25 matches
Shannon Moore: 48 matches (9-38-1) = 19% win
Jim Duggan: 47 matches (26-19-2) = 58% win
Katie Lea: 45 matches (10-33-0 and 2 other matches) = 23% win
Primo Colon: 45 matches (37-8-0) = 82% win
Sho Funaki: 44 matches (8-36-0) = 18% win
Evan Bourne: 41 matches (27-14-0) = 66% win
Layla: 41 matches (4-31-1 and 5 other matches) = 11% win
Paul London: 41 matches (16-25-0) = 39% win
David Hart Smith: 40 matches (14-25-1) = 36% win
Jack Swagger: 40 matches (13-27-0) = 33% win
Jillian Hall: 37 matches (7-26-0 and 4 other matches) = 21% win
Chuck Palumbo: 35 matches (8-24-2 and 1 other match) = 25% win
Manu: 35 matches (19-16-0) = 54% win
Melina: 33 matches (18-13-1 and 1 other match) = 58% win
Cherry: 31 matches (14-14-0 and 3 other matches) = 50% win
Candice Michelle: 30 matches (13-15-0 and 2 other matches) = 46% win
Hornswoggle: 27 matches (14-12-1) = 54% win
Sim Snuka: 27 matches (3-24-0) = 11% win

More than 10 matches
Colin Delaney: 25 matches (6-19-0) = 24% win
Val Venis: 24 matches (7-16-1) = 30% win
Dolph Ziggler: 24 matches (5-19-0) = 21% win
Domino: 23 matches (2-21-0) = 9% win
Kenny Dykstra: 23 matches (6-16-1) = 27% win
Ricky Ortiz: 23 matches (14-9-0) = 61% win
Jay Bradley: 22 matches (1-21-0) = 5% win
Matt Striker: 21 matches (2-19-0) = 10% win
Brie Bella: 20 matches (12-7-0 and 1 other match) = 63% win
Elijah Burke: 20 matches (11-9-0) = 55% win
Ezekiel Jackson: 19 matches (11-8-0) = 58% win
Viscera: 19 matches (4-13-2) = 24% win
Robbie McAllister: 18 matches (0-17-1) = 0% win
Bam Neely: 17 matches (3-14-0) = 18% win
Ric Flair: 17 matches (15-2-0) = 88% win
Armando Estrada: 16 matches (3-13-0) = 19% win
Stevie Richards: 15 matches (5-10-0) = 33% win
Nunzio: 14 matches (1-13-0) = 7% win
unknown: 11 matches (0-11-0) = 0% win

More than 5 matches
Eve: 10 matches (5-1-0 and 4 other matches) = 83% win
Hurricane Helms: 10 matches (3-7-0) = 30% win
Nikki Bella: 10 matches (5-5-0) = 50% win
Rory McAllister: 10 matches (0-10-0) = 0% win
Ashley: 9 matches (3-6-0) = 33% win
Kevin Thorn: 9 matches (0-9-0) = 0% win
Kizarny: 8 matches (8-0-0) = 100% win
Drew McIntyre: 7 matches (1-6-0) = 14% win
Johnny Curtis: 6 matches (6-0-0) = 100% win
KC James: 6 matches (0-6-0) = 0% win

Several matches
Lena: 5 matches (1-0-0 and 4 other matches) = 100% win
Shawn Spears: 5 matches (0-5-0) = 0% win
DJ Gabriel: 4 matches (4-0-0) = 100% win
Jerry Lawler: 4 matches (0-4-0) = 0% win
Tiffany: 4 matches (1-1-0 and 2 other matches) = 50% win
Charles Evans: 3 matches (1-2-0) = 33% win
Chase Stevens: 3 matches (0-3-0) = 0% win
Chris Harris: 3 matches (2-1-0) = 67% win
Colt Cabana: 3 matches (0-3-0) = 0% win
Eric Escobar: 3 matches (1-2-0) = 33% win
Joey Ryan: 3 matches (0-3-0) = 0% win
Vickie Guerrero: 3 matches (1-2-0) = 33% win
Vince McMahon: 3 matches (0-2-1) = 0% win
Goldust: 2 matches (2-0-0) = 100% win
Jason Riggs: 2 matches (0-2-0) = 0% win
Joey Braddock: 2 matches (2-0-0) = 100% win
Josh Daniels: 2 matches (0-2-0) = 0% win
Matt Jackson: 2 matches (0-2-0) = 0% win
Matt Logan: 2 matches (0-2-0) = 0% win
Phil Atlas: 2 matches (0-2-0) = 0% win
Rory Fox: 2 matches (1-1-0) = 50% win
Sal Rinauro: 2 matches (0-2-0) = 0% win
Takeshi Morishima: 2 matches (2-0-0) = 100% win
The Boogeyman: 2 matches (1-1-0) = 50% win

One Shot Stars
Hillary Clinton: 1 match (1 draw)
Adam Armor: 1 match (1 loss) = 0% win
Altar Boy Luke: 1 match (1 loss) = 0% win
Andy Douglas: 1 match (1 loss) = 0% win
Balls Mahoney: 1 match (1 draw)
"Barack Obama": 1 match (1 draw)
Barry Windham: 1 match (1 draw)
Big Daddy Flex: 1 match (1 loss) = 0% win
Brandon Hill: 1 match (1 loss) = 0% win
Brett Badery: 1 match (1 loss) = 0% win
Brian Cage: 1 match (1 loss) = 0% win
Brian Logan: 1 match (1 loss) = 0% win
Bryan Danielson: 1 match (1 win) = 100% win
Carl Oulette: 1 match (1 loss) = 0% win
Chad Collyer: 1 match (1 loss) = 0% win
Charles Robinson: 1 match (1 loss) = 0% win
Cousin Sal: 1 match (1 win) = 100% win
Darren Wade: 1 match (1 loss) = 0% win
David Owens: 1 match (1 loss) = 0% win
Floyd Mayweather: 1 match (1 win) = 100% win
Go Shiozaki: 1 match (1 loss) = 0% win
GQ Gallo: 1 match (1 loss) = 0% win
Greg Cardoza: 1 match (1 loss) = 0% win
James Mason: 1 match (1 win) = 100% win
Jared Ganim: 1 match (1 loss) = 0% win
Jason Styles: 1 match (1 loss) = 0% win
Jay Garland: 1 match (1 loss) = 0% win
Jeff McAllister: 1 match (1 loss) = 0% win
John Cutler: 1 match (1 loss) = 0% win
Jon Davis: 1 match (1 loss) = 0% win
JT Flash: 1 match (1 loss) = 0% win
Julio Dinero: 1 match (1 loss) = 0% win
Karl Wells: 1 match (1 loss) = 0% win
Lawrence Knight: 1 match (1 win) = 100% win
Lenny Lane: 1 match (1 loss) = 0% win
Leroy Kincaid: 1 match (1 loss) = 0% win
Low Ki: 1 match (1 loss) = 0% win
Mae Young: 1 match (1 loss) = 0% win
Marty Garner: 1 match (1 loss) = 0% win
Matt Bentley: 1 match (1 loss) = 0% win
Mega: 1 match (1 loss) = 0% win
Michael Cole: 1 match (1 loss) = 0% win
Mick Foley: 1 match (1 win) = 100% win
Mike Matson: 1 match (1 loss) = 0% win
Mike Rotunda: 1 match (1 draw)
Nick Berk: 1 match (1 loss) = 0% win
Nikolai Volkoff: 1 match (1 draw)
Oliver Biney: 1 match (1 loss) = 0% win
Phil Shatter: 1 match (1 loss) = 0% win
Rob Echoes: 1 match (1 loss) = 0% win
Runjin Singh: 1 match (1 loss) = 0% win
Ryan Taylor: 1 match (1 loss) = 0% win
Scott Reid: 1 match (1 loss) = 0% win
Shawn Rutger: 1 match (1 loss) = 0% win
Steve Anthony: 1 match (1 loss) = 0% win
The Honkytonk Man: 1 match (1 win) = 100% win
the Iron Sheik: 1 match (1 draw)
Tony Atlas: 1 match (1 win) = 100% win
Trish Stratus: 1 match (1 win) = 100% win
Tyrone Jones: 1 match (1 loss) = 0% win
Tyson Tomko: 1 match (1 win) = 100% win
Wayne Costal: 1 match (1 loss) = 0% win

THE WINNERS~!
Triple H: 137 matches (118-15-4) = 89% win
Matt Hardy: 135 matches (101-29-3 and 2 other matches) = 78% win
Michelle McCool: 97 matches (72-23-1 and 1 other matches) = 76% win
the Undertaker: 95 matches (84-7-4) = 92% win
John Cena: 85 matches (65-16-3 and 1 other match) = 80% win
Shawn Michaels: 81 matches (63-14-3 and 1 other match) = 82% win
Kelly Kelly: 73 matches (53-14-0 and 6 other matches) = 79% win
Rey Mysterio Jr.: 72 matches (55-17-0) = 76% win
Bob Holly: 67 matches (53-13-1) = 80% win
Primo Colon: 45 matches (37-8-0) = 82% win
Ric Flair: 17 matches (15-2-0) = 88% win
Eve: 10 matches (5-1-0 and 4 other matches) = 83% win
Kizarny: 8 matches (8-0-0) = 100% win

The Losers~!
MVP: 139 matches (18-116-3 and 2 other matches) = 13% win
Chavo Guerrero Jr.: 123 matches (30-91-1 and 1 other match) = 25% win
Charlie Haas: 91 matches (20-69-2) = 22% win
Victoria: 68 matches (14-46-1 and 7 other matches) = 23% win
Trevor Murdoch: 64 matches (8-55-1) = 13% win
Jimmy Wang Yang: 59 matches (12-46-1) = 21% win
Shannon Moore: 48 matches (9-38-1) = 19% win
Katie Lea: 45 matches (10-33-0 and 2 other matches) = 23% win
Sho Funaki: 44 matches (8-36-0) = 18% win
Layla: 41 matches (4-31-1 and 5 other matches) = 11% win
Jillian Hall: 37 matches (7-26-0 and 4 other matches) = 21% win
Sim Snuka: 27 matches (3-24-0) = 11% win
Colin Delaney: 25 matches (6-19-0) = 24% win
Dolph Ziggler: 24 matches (5-19-0) = 21% win
Domino: 23 matches (2-21-0) = 9% win
Jay Bradley: 22 matches (1-21-0) = 5% win
Matt Striker: 21 matches (2-19-0) = 10% win
Viscera: 19 matches (4-13-2) = 24% win
Robbie McAllister: 18 matches (0-17-1) = 0% win
Bam Neely: 17 matches (3-14-0) = 18% win
Armando Estrada: 16 matches (3-13-0) = 19% win
Nunzio: 14 matches (1-13-0) = 7% win

SINGLES FEUDS
Beth Phoenix VS. Mickie James: 54 singles matches and 32 tag matches.
Chavo Guerrero Jr. VS. CM Punk: 34 singles matches and 7 tag matches.
Mark Henry VS. Matt Hardy: 33 singles matches and 24 tag matches.
Ron Killings VS. Shelton Benjamin: 26 singles matches and 3 tag matches.
Matt Hardy VS. MVP: 23 singles matches and 14 tag matches.
Maryse VS. Michelle McCool: 22 singles matches and 24 tag matches.
Kofi Kingston VS. Shelton Benjamin: 22 singles matches and 4 tag matches.
Kane VS. Rey Mysterio Jr.: 21 singles matches and 12 tag matches.
the Big Show VS. The Undertaker: 21 singles matches and 7 tag matches.
Batista VS. Chris Jericho: 20 singles matches and 16 tag matches.
Batista VS. Edge: 18 singles matches and 13 tag matches.
Chris Jericho VS. Shawn Michaels: 18 singles matches and 9 tag matches.
Triple H VS. Vladimir Kozlov: 17 singles matches and 3 tag matches.
Chavo Guerrero Jr. VS. Kane: 15 singles matches and 10 tag matches.
Jeff Hardy VS. Randy Orton: 15 singles matches and 3 tag matches.
Edge VS. Jeff Hardy: 15 singles matches and 3 tag matches.
MVP VS. Shelton Benjamin: 15 singles matches
JBL VS. John Cena: 14 singles matches and 7 tag matches.
Kofi Kingston VS. Santino Marella: 14 singles matches and 6 tag matches.
Michelle McCool VS. Victoria: 13 singles matches and 25 tag matches.
Chris Jericho VS. JBL: 13 singles matches and 5 tag matches.
Jeff Hardy VS. Vladimir Kozlov: 13 singles matches and 3 tag matches.
Jamie Noble VS. William Regal: 13 singles matches and 3 tag matches.

Tag Matches
Michelle McCool VS. Natalya Neidhart: 37 tag matches.
Ted DiBiase Jr/Cody Rhodes VS. Cryme Tyme: 27+ tag matches. (Cody has 39 tag matches vs JTG.)
Beth Phoenix VS. Mickie James: 32 tag matches.
Jesse/Festus VS. Curt Hawkins/Zach Ryder: 26 tag matches.
Michelle McCool VS. Victoria: 25 tag matches.
Mark Henry VS. Matt Hardy: 24 tag matches.
Maryse VS. Michelle McCool: 24 tag matches.
Maria VS. Natalya Neidhart: 24 tag matches.
John Morrison/Mike Mizanin VS. Jimmy Wang Yang/Shannon Moore: 24 tag matches.
Kelly Kelly VS. Layla: 22 tag matches.
Katie Lee Burchill VS. Mickie James: 21 tag matches.
Cody Rhodes/Hardcore Holly VS. Trevor Murdoch: 21 tag matches.
Maria VS. Maryse: 20 tag matches.
Hardcore Holly VS. Santino Marella: 20 tag matches.
MVP VS. the Undertaker: 20 tag matches.
Jesse/Festus VS. Miz/John Morrison: 20 tag matches.
Cody Rhodes VS. John Cena: 20 tag matches.

For comparison, in 2008 Cena & Orton only had about 15 matches together. By comparison, in 2009 they'd done at least 65 matches.