The Grammy Award for Best Pop Collaboration with Vocals has been handed out since1995. It was known as Grammy Award for Best Pop Vocal Collaboration in the year of its introduction. Van Morrison, Alison Krauss, Carlos Santana and Robert Plant have all won the award twice. Stevie Wonder and Christina Aguilera are the most nominated in this category with six nominations each.

Winners: Grammys Best Pop Collaboration with Vocals

Year
Winner/s
Song
2009
Robert Plant & Alison Krauss
"Rich Woman"
2008
Robert Plant & Alison Krauss
"Gone Gone Gone (Done Moved On)"
2007
Tony Bennett & Stevie Wonder
"For Once in My Life"
2006
Gorillaz & De La Soul
"Feel Good Inc"
2005
Ray Charles & Norah Jones
"Here We Go Again"
2004
Sting & Mary J. Blige
"Whenever I Say Your Name"
2003
Santana & Michelle Branch
"The Game of Love"
2002
Christina Aguilera, Lil' Kim, Mya & Pink
"Lady Marmalade"
2001
B. B. King & Dr. John
"Is You Is, or Is You Ain't (My Baby)"
2000
Rob Thomas & Santana
"Smooth"
1999
Burt Bacharach & Elvis Costello
"I Still Have That Other Girl"
1998
John Lee Hooker & Van Morrison
"Don't Look Back"
1997
Natalie Cole & Nat King Cole
"When I Fall in Love"
1996
The Chieftains & Van Morrison
"Have I Told You Lately"
1995
Al Green & Lyle Lovett
"Funny How Time Slips Away"