...Baby One More Time produced five singles. The lead single, "...Baby One More Time", brought Spears tremendous global success, reaching number one in most countries it charted in and becoming one of the best-selling physical singles of all time. In 2020, it was named the greatest debut single of all time by Rolling Stone. Subsequent singles "Sometimes" and "Born to Make You Happy" peaked within the top ten in most international countries while "(You Drive Me) Crazy" became Spears's second US Billboard Hot 100 top-ten hit. Spears heavily promoted the album through interviews and televised performances. Furthermore, she embarked on her first headlining concert tour, entitled ...Baby One More Time Tour (1999) and later continued with (You Drive Me) Crazy Tour (2000).

Oops!... I Did It Again produced four singles. The title track was a global commercial success, reaching number one in 17 countries and peaking at number nine on the US Billboard Hot 100. "Lucky" peaked within the top ten in 16 countries, but only at number 23 on the US Billboard Hot 100. "Stronger" peaked at number 11 on the US Billboard Hot 100 and became the best-selling single from the album. The final single "Don't Let Me Be the Last to Know" was moderately successful across Europe and failed to chart altogether in the United States. To promote the album, Spears performed on several television shows and award ceremonies, including a controversial performance at the 2000 MTV Video Music Awards, also hosting and performing for the first time on Saturday Night Live. Furthermore, she embarked on her third concert tour, entitled the Oops!... I Did It Again Tour (2000).

Britney produced six singles. "I'm a Slave 4 U" reached the top ten in 20 countries but peaked only at number 27 on the US Billboard Hot 100, becoming Spears's first lead single not to peak within the top ten. "Overprotected" also achieved international commercial success but peaked only at number 86 the US Billboard Hot 100. "I'm Not a Girl, Not Yet a Woman", "I Love Rock 'n' Roll" and "Boys" reached the top ten in several countries but all failed to enter the US Billboard Hot 100, while "Anticipating" was released exclusively in France instead of "I Love Rock 'n' Roll". To further promote the album, Spears embarked on her fourth concert tour, titled Dream Within a Dream Tour, from November 2001 until July 2002.

In the Zone was promoted with four singles. "Me Against the Music", featuring Madonna, reached the top ten in nearly every country except the United States, where it only peaked at number 35 on the Billboard Hot 100. "Toxic" peaked atop the charts in eight countries and at number nine on the Billboard Hot 100, becoming Spears' first US top-ten hit since "Oops!... I Did It Again" (2000), and won Spears her first Grammy Award. "Everytime" peaked at number 15 on the US Billboard Hot 100 and within the top ten nearly everywhere else. "Outrageous" was plagued by a lack of promotion due to Spears injuring her knee while filming its accompanying music video, and only peaked at number 79 on the US Billboard Hot 100. To further promote the album, Spears embarked on the Onyx Hotel Tour (2004).

Blackout produced three singles. "Gimme More" peaked at number three on the US Billboard Hot 100, becoming her highest-peaking single on the chart since "...Baby One More Time" (1998), and reached the top ten in additional 16 countries. "Piece of Me" peaked at number 18 on the Billboard Hot 100, but replicated the international commercial success of its predecessor. Its accompanying music video won Spears her first MTV Video Music Award, winning Video of the Year, Best Female Video and Best Pop Video in 2008. "Break the Ice" did not fare as well as its predecessors, peaking at number 43 on the Billboard Hot 100. Originally intended as the fourth single, "Radar" was later included on Spears' following studio album Circus and was released as its fourth and final single in June 2009.