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This is a list of notable events in country music that took place in the year 1999.

• March 6 —George Jones, in the midst of a comeback this year, is seriously injured when he crashed his Lexus into a bridge. It is later revealed that alcohol was a factor in the accident, and he pleaded guilty to drunk driving charges.
• June — ComedianJeff Foxworthy debuts his syndicated radio countdown show, "The Foxworthy Countdown." The radio show would end ten years later.
• September 4 —Lonestar's hit, "Amazed", spends its eighth week at No. 1 on theBillboard magazineHot Country Singles & Tracks chart, becoming the first song to do so sinceJack Greene's 1966 hit, "There Goes My Everything." In several other trade magazines, includingRadio & Records, "Amazed" reigns for nine weeks, which made it the longest-lasting Number One single since 1966's "Almost Persuaded" byDavid Houston. By year's end, "Amazed" is gaining popularity onCHR andadult contemporary stations (in re-mixed versions, which excised the steel guitar).
• September 22 -Alan Jackson sings the chorus ofGeorge Jones' "Choices" in the middle of his performance of "Pop a Top" on theCountry Music Association Awards broadcast, after TV producers required that Jones perform an abridged version, in which he refused and boycotted the show. The performance has become one of the best and most memorable moments in CMA history.
• September 28 -Garth Brooks releasesIn the Life of Chris Gaines, a compilation album of Brooks' alter ego, fictional Australian rock starChris Gaines. The album was intended to be the soundtrack to a film calledThe Lamb, however the film was never filmed, due to financial and management problems. The album received disappointing sales in comparison to Brooks' other albums.

• May 3 –Ella Langley, rising singer-songwriter of the 2020s ("You Look Like You Love Me")

• February 8 –Lulu Belle (born Myrtle Eleanor Cooper), 85, one-half of the 1930s–1940s husband-and-wife duo Lulu Belle and Scotty, later a state Representative in the North Carolina Legislature.
• September 30 —Connie Eaton, 49, singer of the 1970s (cancer)
• October 2 —Danny Mayo, 49, writer of hit singles byAlabama,Confederate Railroad,Pirates of the Mississippi, andTracy Byrd, father of songwriterAimee Mayo (heart attack)
• December 17 —Rex Allen, 78, "The Arizona Cowboy" and traveling rodeo performer.
• December 20 —Hank Snow, 85, "The Singing Ranger," best known for "I'm Movin' On."

• Kenny Baker

• Johnny Bond (1915–1978)
• Dolly Parton (born 1946)
• Conway Twitty (1933–1993)

• Ronnie Prophet
• Walt Grealis

• Best Female Country Vocal Performance — "Man! I Feel Like a Woman!",Shania Twain
• Best Male Country Vocal Performance — "Choices",George Jones
• Best Country Performance by a Duo or Group with Vocal — "Ready to Run",Dixie Chicks
• Best Country Collaboration with Vocals — "After the Gold Rush",Emmylou Harris,Dolly Parton andLinda Ronstadt
• Best Country Instrumental Performance — "Bob's Breakdowns",Tommy Allsup,Asleep at the Wheel,Floyd Domino,Larry Franklin,Vince Gill andSteve Wariner
• Best Country Song — "Come on Over", Shania Twain andRobert John "Mutt" Lange
• Best Country Album —Fly, Dixie Chicks
• Best Bluegrass Album —Ancient Tones,Ricky Skaggs & Kentucky Thunder

• Best Country Male Artist —Paul Brandt
• Best Country Female Artist —Shania Twain
• Best Country Group or Duo —The Rankins

• Entertainer of the Year —Shania Twain
• Song of the Year — "Amazed",Marv Green,Aimee Mayo
• Single of the Year — "Amazed",Lonestar
• Album of the Year —Fly,Dixie Chicks
• Top Male Vocalist —Tim McGraw
• Top Female Vocalist —Faith Hill
• Top Vocal Duo or Group — Dixie Chicks
• Top New Male Vocalist —Brad Paisley
• Top New Female Vocalist —Jessica Andrews
• Top New Vocal Duo or Group —Montgomery Gentry
• Video of the Year — "Breathe", Faith Hill (Director:Lili Fini Zanuck)
• Vocal Event of the Year — "When I Said I Do",Clint Black withLisa Hartman Black

(presented in Sydney on October 12, 1999)

• Best Country Album -The Captain (Kasey Chambers)
• ARIA Hall of Fame -Jimmy Little

• CMT Maple Leaf Foods Fans' Choice Award —Shania Twain
• Male Artist of the Year —Paul Brandt
• Female Artist of the Year — Shania Twain
• Group or Duo of the Year —The Wilkinsons
• SOCAN Song of the Year — "26 Cents", Steve Wilkinson, William Wallace
• Single of the Year — "26 Cents", The Wilkinsons
• Album of the Year —Nothing but Love, The Wilkinsons
• Top Selling Album —Wide Open Spaces,Dixie Chicks
• Video of the Year — "That Don't Impress Me Much", Shania Twain
• Wrangler Rising Star Award — The Wilkinsons
• Vocal/Instrumental Collaboration of the Year — "From This Moment On", Shania Twain andBryan White

• Entertainer of the Year —Shania Twain
• Song of the Year — "This Kiss", Robin Lerner,Annie Roboff andBeth Nielsen Chapman
• Single of the Year — "Wide Open Spaces",Dixie Chicks
• Album of the Year —A Place in the Sun,Tim McGraw
• Male Vocalist of the Year — Tim McGraw
• Female Vocalist of the Year —Martina McBride
• Vocal Duo of the Year —Brooks & Dunn
• Vocal Group of the Year — Dixie Chicks
• Horizon Award —Jo Dee Messina
• Music Video of the Year — "Wide Open Spaces", Dixie Chicks (Director: Thom Oliphant)
• Vocal Event of the Year — "My Kind of Woman, My Kind of Man",Vince Gill andPatty Loveless
• Musician of the Year —Randy Scruggs

• Canadian Country Artist of the Year —Shania Twain
• Best Country Album —Nothing but Love,The Wilkinsons
• Best Country Single — "26 Cents", The Wilkinsons
• Male Artist of the Year —Paul Brandt
• Female Artist of the Year — Shania Twain
• Group of the Year —The Wilkinsons
• Outstanding New Male Artist —Gil Grand
• Outstanding New Female Artist —Stephanie Beaumont
• Outstanding New Group or Duo —The Johner Brothers
• Canadian Country Video — "26 Cents", The Wilkinsons
• Top Country Composer(s) —Bruce Guthro

• Whitburn, Joel, "Top Country Songs 1944–2005 – 6th Edition." 2005.

• Country Music Association
• Inductees of the Country Music Hall of Fame

• Country Music Hall of Fame

• 1999 in music
• Country music by year

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