P. Diddy Awards

1997
MTV Video Music Award for Best R&B Video ("I'll Be Missing You")

Rolling Stone Magizines Readers Best Rap Artist of the Year

Rolling Stone Magizines Critics Artist of the Year.

1998
2 Grammy Awards for Best Rap Performance by a Duo or Group ("I'll Be Missing You" (with Faith Evans and 112)) and Best Rap Album (No Way Out)

MTV Video Music Award for Viewer's Choice ("It's All About The Benjamins")

2 Soul Train Music Awards for Best R&B/Duo or Rap Music Video ("I'll Be Missing You") and the Sammy Davis, Jr. Award for 'Entertainer of the Year,

2 Kid's Choice Awards for Best Dresser and Favorite Singer

2 World Music Awards for World's Best-Selling Rap Artist/Group and World's Best-Selling New Artist.

2001
VH1/Vogue Fashion Award for Sharp Dressed Man.

2003
2 Soul Train Music Award for R&B/Soul Single Group, Band or Duo ("Bump Bump Bump" with B2K)

Radio Music Award for Best Driving Song ("Shake Ya Tailfeather" with Nelly and Murphy Lee).

Vibe Award for Style Maverick Award

2004
Grammy Award for Best Rap Performance by a Duo or Group ("Shake Ya Tailfeather" with Nelly and Murphy Lee).