Regis Chakabva's path in cricket took him through Highfields, Churchill, on to Takashinga, and finally a Twenty20 against Pakistan and an ODI debut against Kenya, and he is regarded as a wicketkeeper of high promise in selection circles. Chakabva represent Zimbabwe Under-19s at the Afro-Asia Under-19 Cup in 2005, but despite the rebel crisis and subsequent player drain, slipped behind Tatenda Taibu, Brendan Taylor, and Alester Maregwede in the national wicketkeeping stakes and has struggled to force his way ahead of them.

With Maregwede concentrating on his batting at the time, Chakabva took up the gloves for Zimbabwe A during the South African Academy's visit in 2007. He kept wicket for Zimbabwe Provinces in the SAA Provincial One-day Challenge in 2008 and also proved one of their most consistent batsmen in the competition as he scored 62, 66, 60 and 118 in consecutive innings against Northerns and Namibia. He gave up the gloves when Taibu returned for the MTN Domestic Championsip, but continued to contribute in the middle order, his 71 taking Zimbabwe to a three-wicket win over the Cape Cobras in the competition.

Despite a disappointing run during the Pakistan Cricket Academy's visit in 2008 he was included in Zimbabwe's squad for their trip to Canada soon afterwards and made his international debut in a Twenty20 against Pakistan at King City. He was anonymous in the match as Zimbabwe lost by seven wickets, a specialist batsman at No. 8, but got another chance during the Kenya Tri-Nation tournament soon afterwards. On his one-day international debut against the hosts he scored 41 down the order as Zimbabwe lost heavily in the third match.

Chakabva had been with Northerns under the old domestic system, and with the re-structuring of Zimbabwe's domestic system, continued as Mashonaland Eagles' wicketkeeper. He continues to remain on the fringes of national selection, and was part of the Zimbabwe XI squad that toured Netherlands and Canada in 2010.