From Harare, Masakadza is the youngest of three brothers who have each played cricket at high levels – the others are Hamilton (born 1983) and Shingirai Masakadza (born 1986), who have both played Test cricket for Zimbabwe's national side. A left-handed batsman and slow left-arm orthodox spinner, Wellington Masakadza represented the Zimbabwean under-19s at the 2012 Under-19 World Cup, playing in three matches. He made his senior debut for the Mountaineers franchise during the 2013–14 domestic season, having performed well in four trial Twenty20 games played prior to the start of the season.

Masakadza went on to play five matches in the 2013–14 Logan Cup, taking 15 wickets. This included figures of 5/63 on his first-class debut, against the Matabeleland Tuskers.^[9] In September 2014, he was selected for the Zimbabwe A that toured Bangladesh, playing in two first-class and three one-day games.^[5][6] Masakadza took 6/63 in the first of those matches, his best figures.^[10] He subsequently selected in the Zimbabwean senior team's 17-man Test squad for its tour of Bangladesh in October and December, along with both of his brothers, although he did not participate in any of the Tests.^[11] For the 2014–15 Zimbabwean season, Masakadza switched to play for the Mashonaland Eagles.^[5]

He made his One Day International debut for Zimbabwe against Ireland on 9 October 2015, but could not do impact on the series. During the Afghanistan tour of Zimbabwe, he took 4 for 21 runs, finally Zimbabwe won the match convincingly by 8 wickets. Masakadza was adjudged as the man of the match.^[12]