Shingirai Winston Masakadza (born 4 September 1986) is a cricketer and former professional footballer from Zimbabwe. The brother of former Zimbabwe cricket captain Hamilton Masakadza, he is a pace bowler and middle-order batsmen. After making his first class debut for Easterns in 2008, he was called up to the Zimbabwe squad to face the West Indies in the Caribbean in February 2010. Before becoming a full-time cricketer, Massakadza played football for Dynamos, one of Zimbabwe's most popular clubs.