Here are the nominees. Which records deserved to win? What's missing? Note: After 1993 a separate category for one time collaborations was added. This thread only lists the pop group/duo category as it is named at the awards.

1989:

Don't Know Much- Linda Ronstadt Aaron Neville- WINNER- (she recorded with him to give his career a boost and he far eclipsed her in popularity thereafter)
Love Shack- B52s
She Drives Me Crazy- Fine Young Cannibals
The Living Years- Mike and the Mechanics
If You Don't Know Me By Now- Simple Red

IMO: Don't Know Much wasn't a bad choice.

1990:

All My Life- Linda Ronstadt/Aaron Neville- WINNER (they thought they had no chance of winning so they stayed home on award night)
Hold On- Wilson Phillips (Billboard's #1 pop chart single of that year)
All I Wanna Do is Make Love to You- Heart
Across the River- Bruce Hornsby and the Range
Roam- B52s
Unchained Melody- Righteous Brothers


IMO: Wilson Phillips were big, but I guess in hindsight All My Life showed a bit more talent

MISSING: This Old Heart of Mine- Rod Stewart/Ron Isley, Don't Hold Back Your Love- Hall and Oates

1991:

Losing My Religion- REM- WINNER
The Commitments soundtrack
More than Words- Extreme
Right Here Right Now- Jesus Jones (this later became the theme for a car commercial)
You're in Love- Wilson Phillips

IMO: Wilson Phillips should have won

MISSING: Thinking About You- Londonbeat, The First Time-Surface

1992:

Beauty and the Beast- Peabo Bryson/Celine Dion- WINNER
Sometimes Love Just Aint Enough- Patti Smyth/Don Henley
Diamonds and Pearls- Prince and the NPG
Dont Let the Sun Go Down On Me- Elton John/George Michael
I Can't Dance- Genesis

IMO: I guess Peabo and Celine were the best, though Prince was decent too

MISSING: Stars- Simply Red

1993:

A Whole New World- Peabo Bryson/Regina Belle- WINNER
Man on the Moon- REM
Music of the Night- Michael Crawford/Barbra Streisand
When I Fall in Love- Celine Dion/Clive Griffin
Love is- Vanessa Williams/Brian McKnight

IMO: Belle and Bryson won were probably the best of the lot, though I like it less and less as time passes. Love Is wasn't bad

1994:

I Swear- All4One- WINNER
Stay(I Missed You)- Lisa Loeb and Nine Stories
Mmmm Mmmm Mmmm Mmmm- Crash Test Dummies
The Sign- Ace of Base
I'll Stand By You- Pretenders

IMO: Pretenders were the only vets here, not a bad record

MISSING: Love is All Around- Wet Wet Wet, Because the Night- 10,000 Maniacs

1995:

Let Her Cry- Hootie and the Blowfish- WINNER
I Can Love You Like That- All4One
Waterfalls- TLC
I'll Be There for You- Rembrandts
Love Will Keep Us Alive- Eagles

IMO: Of this bunch the Eagles were the best, Hold My Hand was a more definitive Hootie single which I guess was ineligible because it came out in 94 though it became a hit in mid95.

MISSING: I Believe- Blessid Union of Souls, Back for Good-Take That, Roll to Me- Del Amitri

1996:

Free As A Bird- Beatles
Peaches- Presidents of the United States of America
When You Wish Upon A Star- Take-6
Neville Brothers- forgot the record
Gin Blossoms- forgot the record
When You Love A Woman

IMO: Beatles were chosen for purely sentimental catch-up reasons, if Gin Blossoms' entry was Follow You Down or Til I Hear it From You they should've won

MISSING: Old Man and Me (When I Get to Heaven)- Hootie and the Blowfish, All Along- Blessid Union of Souls, The Earth the Sun the Rain- Color Me Badd

1997:

Virtual Insanity- Jamiroquai- WINNER
Has Anybody Seen My Baby- Rolling Stones
MmmmBop- Hanson
Don't Speak- No Doubt
Silver Springs- Fleetwood Mac

IMO: I guess Jamiroquai were the best of this list, Hanson was Ok but their lyrics are undecipherable

1998:

Jump Jive and Wail- Bryan Setzer Orchestra- WINNER
Don't Want to Miss A Thing- Aerosmith
Iris- Goo Goo Dolls
One Week- Barenaked Ladies
forgot the other entry

IMO: Setzer was certainly going against the grain so not a poor choice. Aerosmith's record is the only one they ever did that I like

MISSING: A Promise Aint Enough- Hall and Oates, A Promise I Make- Dakota Moon

1999:

Maria Maria- Santana- WINNER
Unpretty- TLC
All Star- Smash Mouth
I Want it That Way- Backstreet Boys
Kiss Me- Sixpence None the Richer

IMO: Santana's record is OK but it's in the wrong category should have been in either r&b group or pop collab since it features the Product G&B who went unrewarded for their singing, Backstreet Boys or Smash Mouth should have won instead

MISSING: The Hardest Thing- 98 Degrees

2000:

Cousin Dupree- Steely Dan
Bye Bye Bye- NSync
Show Me the Meaning of Being Lonely- Backstreet Boys
Breathless- Corrs
Pinch me- Barenaked Ladies

IMO: Don't like any of these records, to me It's Gonna Be Me was a more interesting NSync record than Bye Bye Bye

MISSING: I Knew I Loved You- Savage Garden would have been a good winner, Back Here- BBMak

2001:

Stuck In A Moment You Can't Get Out Of- U2- WINNER
Superman) It's Not Easy- Five for Fighting
Imitation of Life- REM
Gone -NSync
Shape of My Heart- Backstreet Boys

IMO: U2 deserved it, I guess the grammys didn't realize that Five for Fighting isn't a group

MISSING/MISCATEGORIZED: Train's Drops of Jupiter was nominated in rock but was really a pop record and should've been nominated here instead, If You're Gone- Matchbox20 was all over the radio this year but wasn't nominated though the album Mad Season was up for raock album

2002:

Hey Baby- No Doubt- WINNER
Where Are You Going- Dave Matthews Band
Girlfriend -NSync
Bon Jovi- forgot the record
forgot the other entry

IMO: Don't like No Doubt but I guess they deserved it out of this lot

MISSING: Do it for Love- Hall and Oates

2003:

Underneath it All- No Doubt- WINNER
Hole in the World- Eagles
Unwell- Matchbox20
Misunderstood- Bon Jovi
Stacy's Mom- Fountains of Wayne

IMO: No Doubt's win seems repetitive. Matchbox20 gets my vote

MISCATEGORIZED: Train's Calling All Angels is pop not rock and should've shown up here instead of in rock group

OVERALL: To me this category got dull once they filtered out the one-shot collaborations. I'll post that category once I remember all the entries some of which were quite obscure

Steely Dan won for 2000

1989: I think I'd go for Mike & The Mechanics, Living Years is a real tearjerker if you've lost a parent. I love Linda Ronstadt's 70's and early 80's material, but nothing after the What's New Album

1990: Hold On was a GREAT record. Heart's my fave act listed, but All I Wanna Do wasn't one of their classics

1991: Losing My Religion was great, R.E.M. deserved it.

1992: Diamonds and Pearls was a great Prince song which actually received AC airplay, something he never had until that point

1993: this entire list was pretty blah to me, tho R.E.M. would get it by default to me

1994: quite a bit better than the previous year, I'd give it to Lisa Loeb

1995: TLC should've won it

1996: I think Beatles probably had the best song of the lot

1997: Fleetwood Mac's song was the best, but technically it was from 1976, so I'd have given it to No Doubt

1998: kind of a blah-list. I guess Barenaked Ladies.

1999: TLC should've won it

2000: I guess N'Sync. They were popular before, but Bye Bye Bye was when they officially "arrived"

2001: R.E.M.'s song was my fave from this list

2002: I think No Doubt deserved it, tho Everyday was probably Bon Jovi's best rock song since the New Jersey album

2003: Fountains Of Wayne, loved them since 96 and Stacy's Mom was such a catchy new-wave ditty