
In August and October 1999, Khanna performed in the Awesome Foursome concert held at the Shah Alam Outdoor Stadium, Malaysia and the Magnificent Five concert at Birmingham, England. It featured her opposite Fardeen Khan and was an average grosser at the box office.

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Her last film was Love Ke Liye Kuch Bhi Karega (2001), a remake of the Telugu movie Money (1993). She left the industry after her marriage to Akshay Kumar in 2001, citing that she did not enjoy the acting profession any more. Film director Karan Johar admitted in an interview that Khanna was in his mind for the role of Tina in Kuch Kuch Hota Hai, but she refused it, and thus Rani Mukerji was signed. Her acting in the film met with poor reviews. She also acted in the David Dhawan-directed comedy Jodi No.1 (2001). Chal Mere Bhai (2000) featured Khanna in a special appearance beside a leading role in the comedy Joru Ka Ghulam, opposite Govinda.

Similar to The Seven Samurai in story, it was an average grosser at the box office. She was paired opposite Aamir Khan in Dharmesh Darshan's Mela (2000). In the same year, she acted opposite Saif Ali Khan in Yeh Hai Mumbai Meri Jaan, a romantic comedy directed by Mahesh Bhatt. Khanna played the lead role in Baadshah (1999), featuring Shah Rukh Khan as a detective. She was paired with Daggubati Venkatesh in the Telugu film Seenu (1999). In the former she played a news reporter who falls in love with a criminal whom she interviews. Khanna acted opposite Akshay Kumar in two action films: International Khiladi and Zulmi (both 1999). Her only release in 1998 was Jab Pyaar Kisise Hota Hai, which featured her as Salman Khan's love interest and was a box office success. Both of these films were poor box office performers. While reviewing Dil Tera Diwana, Vijiyan wrote about Khanna: "Unlike her previous movies, she looks really good in all her scenes and she can act well." In 1997, two films featuring her Uff! Yeh Mohabbat and Itihaas were released. Vijiyan of the New Straits Times wrote that "Khanna does not look like a typical Hindi actress". Jaan was a box office hit and Dil Tera Deewana failed to do well. The following year she played lead roles in Raj Kanwar's action film Jaan and Lawrence D'Souza's romance Dil Tera Diwana opposite Ajay Devgn and Saif Ali Khan respectively. It performed well at the box office and became the sixth-highest-grossing film of the year, and she received the Filmfare Award for Best Female Debut for her performance. She was cast by Dharmendra and before the film's release Khanna signed for two more projects. Khanna made her screen debut opposite Bobby Deol in Rajkumar Santoshi's romance Barsaat (1995). Before beginning her film career, Khanna went through an eye surgery.

After finishing her Class 12th, she wanted to pursue a career as chartered accountant and gave the entrance examination but joined the film industry instead on the insistence of her parents.

Khanna attended the New Era High School, Panchgani and the Narsee Monjee College of Commerce and Economics. Her sister Rinke Khanna and cousin Karan Kapadia have also acted in films. On her mother's side, she was the niece of Simple Kapadia, an actress and costume designer whom she "adored". Her maternal grandfather, Chunnibhai Kapadia was a Gujarati businessman and her father Rajesh Khanna, born in Punjabi Khatri in Amritsar, Punjab, was from a family of railway contractors. Twinkle Khanna was born on 29 December 1973 in Mumbai, the first of two daughters of veteran Hindi film actors Dimple Kapadia and Rajesh Khanna, with whom she shared her birthday. She is the daughter of famous Bollywood actor Rajesh Khanna and famous actress Dimple Kapadia. In 2019, Khanna launched Tweak India, a bilingual digital media platform for women. Her most recent book and first novel, Pyjamas Are Forgiving (Juggernaut Books, 2018) made her the highest-selling female author in India in the year 2018, according to Nielsen BookScan India. Funnybones Movies which was set up in 2016. Her second book, The Legend of Lakshmi Prasad, a collection of short stories, one of which was based on social entrepreneur Arunachalam Muruganantham was later made into National Award-winning feature film, Pad Man with the focus on dispelling taboos around menstruation It was produced under Khanna's production house Mrs. In 2015, she released her first non-fiction book, MrsFunnybones which was declared a bestseller, making Khanna India's highest-selling woman writer that year. Twinkle Khanna (also known as Tina Jatin Khanna born on 29 December 1974) is a well-known author, newspaper columnist, interior designer, film producer and a former film actress.
