In February 2000, aged just 16 and still a schoolboy at Churchill Boys High School, he became the first black Zimbabwean to score a first-class century. Soon after, in July 2001 he became the youngest player to make a century on his Test debut. His innings of 119 was made against the West Indies in Harare and helped his side draw the match. Still at high school, he was aged just 17 years and 254 days at the time. He only held this record until August however when Mohammad Ashraful took it from him.
He went into the record books again against the West Indies in December 2007, this time in an ODI. His opening partnership of 167 with Vusi Sibanda was a national record, with Masakadza making 80 of those runs. His maiden ODI century against a Test-playing nation came on 14 August 2009, eight years after his Test century, when he scored 102 off 112 balls against Bangladesh batting at Number three.
He is also the first Zimbabwean to have two ODI scores of more than 150, both coming in one week when he scored 156 and 178 not out against Kenya in October 2009 in the first and fifth matches in Harare.
When Zimbabwe returned to Test cricket in 2011, Masakadza was selected to play in each of the one-off Tests against Bangladesh, Pakistan and New Zealand. Batting at number three, he scored a century in the first innings of the Bangladesh Test, the second of his Test career, and Zimbabwe went on to win the match.