Saif was meant to make his debut in Bekhudi (1992) opposite Kajol but the film took off without him.

In 1993, he made his Bollywood debut in the film Parampara. For his next film Aashiq Awara, which also released that year, he won the Filmfare Best Male Debut Award. His breakthrough role came in 1994 with Yeh Dillagi starring opposite Kajol and Akshay Kumar which was his first major hit. Khan went on to star in many films but they failed at the box office. He only had success with multi-starrer hits like Main Khiladi Tu Anari (1994), Imtihaan (1995), Kachche Dhaage (1999) and Hum Saath-Saath Hain: We Stand United (1999). After some box office failures he had a hit with the film Kya Kehna (2000).

His acting career, more or less, went through a relative slump until 2001, when he was cast in Farhan Akhtar's hit film, Dil Chahta Hai, which was an Aamir Khan starrer. He received much acclaim for his role as Sameer with critic Taran Adarsh calling it his career-best performa