The youngest in a family of five children, Raina decided to take up cricket seriously in 1999, and moved from his home town of Ghaziabad, near New Delhi to Lucknow, the capital of Uttar Pradesh, to attend the specialist government Sports College.He happens to be the second Kashmiri pandit to play for India. He rose to become the captain of the Uttar Pradesh U-16s came to prominence amongst Indian selectors in 2002, when he was selected at the age of 15 and a half years for the U-19 tour to England, where he made a pair of half-centuries in the U-19 Test matches. He toured Sri Lanka later that year with the U-17 team. He made his Ranji Trophy debut for Uttar Pradesh against Assam in February 2003 at the age of 16, but did not play another match until the following season. In late 2003, he toured Pakistan for the U-19 Asian ODI Championship before being selected for the 2004 U-19 World Cup, where he scored three half centuries, including a 90 scored off only 38 balls. He was then awarded a Border-Gavaskar scholarship to train at the Australian Cricket Academy and in early 2005, he made his first-class limited overs debut, and scored 645 runs that season at an average of 53.75. He was selected to participate in the Challenger Series in early 2005, and after injury to Sachin Tendulkar and suspension to captain Sourav Ganguly, Raina was selected for the Indian Oil Cup 2005 in Sri Lanka