The Zimbabwe national cricket team toured South Africa in October and November 1999 and played one Test match against the South Africa national cricket team. They also competed in the 2000 Standard Bank Triangular Tournament in January and February, playing six One Day International (ODI) matches against South Africa and England. This was the first time that Zimbabwe had toured to South Africa, although teams from both Zimbabwe and Rhodesia had played in South Africa as part of South African domestic cricket.Ward J A brief history of Zimbabwe cricket, CricInfo. Retrieved 17 April 2018.

Immediately before Zimbabwe travelled to South Africa they had played a Test and ODI series against Australia who had toured Zimbabwe for the first time. The matches saw Zimbabwe defeated heavily.Conn M (2001) Australia in Sri Lanka and Zimbabwe, 1999–2000, Wisden Cricketers' Almanack, 2001. Retrieved 12 July 2023. After the single Test match in South Africa the South Africans travelled to Zimbabwe and played a return Test match at Harare with only a fortnight separating the matches.The Zimbabweans in South Africa, 1999–2000, Wisden Cricketers' Almanack, 2001. Retrieved 15 December 2019.

South Africa won the Test match convincingly and Zimbabwe finished last in the ODI tournament. At the end of the ODI tournament England travelled to Zimbabwe to play four ODIs against Zimbabwe.with only a fortnight separating the matches.Bateman C (2001) England in South Africa and Zimbabwe, 1999–2000, Wisden Cricketers' Almanack, 2001. Retrieved 12 July 2023.

Tour party The Zimbabwe team was captained by Alistair Campbell. This was Campbell's last Test as captain of Zimbabwe; he resigned a week after the Test match and was replaced, initially in an interim role, by Andy Flower.Tour of South Africa 1999–00 , Test Cricket Tours. Retrieved 14 April 2018. Fast bowler Heath Streak, who had originally been selected for the tour, was injured and replaced by Andy Blignaut. Blignaut then pulled a muscle whilst practicing and was replaced by Pommie Mbangwa. Leg-spinner Paul Strang was injured and unavailable for the tour. David Mutendera was the only uncapped member of the tour party but did not play in the Test match.

The South African team was captained by Hansie Cronje.

Test match The Test match was the first to be played at Springbok Park in Bloemfontein and only the second between the two countries.Manthorp N (2001) Test Match, South Africa v Zimbabwe, 1999–2000, Wisden Cricketers' Almanack, 2001. Retrieved 14 April 2018.Chesterfield T (1999) Bacher injury mishap on eve of Test, CricInfo, 29 October 1999. Retrieved 16 April 2018. Zimbabwe had been soundly beaten by Australia and without Streak and Paul Strang were fielding a weakened team.Zimbabwe seek to redeem lost pride, CricInfo, 29 October 1999. Retrieved 16 April 2018.Chesterfield T (1999) Elworthy snubbed and SABC finally admit summer has arrived, CricInfo, 28 October 1999. Retrieved 16 April 2018. They were reduced to 79/6 before a half-century by Guy Whittall restored some respectability, although their score of 192 "looked woefully inadequate". South Africa scored 417 against the weakened Zimbabwean bowling attack, with Neil Johnson, who had gone into the match with an injury, unable to bowl more than two overs for the visitors. Jonty Rhodes top-scored with 70 runs for South Africa whilst Hansie Cronje became the leading South African run scorer in Test matches during his innings of 64.Chesterfield T (1999) Cronje establishes batting milestone, CricInfo, 31 October 1999. Retrieved 16 April 2018.

Zimbabwe again lost their first six wickets for a low score, 123 in this instance, before the tail-end batsmen were able to add runs against Paul Adams' spin bowling, Whittall scoring his second half-century of the match. Adams finished with four wickets as Zimbabwe were bowled out for 212, losing the match by an innings and 13 runs on the fourth day.Chesterfield T (1999) Adams help South Africa wrap up first Test, CricInfo, 2 November 1999. Retrieved 16 April 2018.

Standard Bank Triangular Tournament

During January and February 2000 Zimbabwe returned to South Africa to play in the 2000 Standard Bank Triangular Tournament, a One Day International series played between Zimbabwe, South Africa and England, who had just completed a tour of South Africa. The matches were all played over 50-overs with four of Zimbabwe's six matches played under floodlights. South Africa were considered by far the strongest of the three teams and started the tournament as clear favourites.Standard Bank International Series, 1999–2000, Wisden Cricketers' Almanack, 2001. Retrieved 16 April 2018.

Heath Streak returned to the Zimbabwe squad for the tournament having recovered his fitness. Gary Brent, Stuart Carlisle, Everton Matambanadzo and Craig Wishart all returned to the squad, with Trevor Gripper, David Mutendera, Gavin Rennie and Bryan Strang all being left out. Andy Flower retained the captaincy.

After losing to South Africa in the opening match of the tournament, Henry Olonga "destroyed" England's batting in the second match. Olonga, who was the first black Zimbabwean to play for the national team aged 17 in 1995, took six wickets for 19 runs in the match, his best bowling figures in List A cricket.Ward J (2000) Henry Olonga – Zimbabwe's match winner, CricInfo, 18 February 2000. Retrieved 16 April 2018.Henry Olonga, CricInfo. Retrieved 16 April 2018. Zimbabwe won the match by 102 runs but lost to England in their next match before narrowly beating South Africa by two wickets in the second meeting between the two teams, Heath Streak scoring the winning run off the last ball of the innings after Andy Flower and Guy Whittall had put on 91 runs in a record Zimbabwean 7th wicket partnership.6th match, South Africa v Zimbabwe 1999–2000, Standard Bank International Series 1999–2000, Wisden Cricketers' Almanack, 2001. Retrieved 16 April 2018.

After each team had played four matches Zimbabwe were top of the table on run rate, each team having won two and lost two of their matches. A loss to South Africa in the third meeting between the teams, left their final match against England, the last of the group stage, as a winner-takes-all semi-final, the winner qualifying for the final. The match was rained off and England qualified on net run rate for the final where they lost to South Africa.

Other matches Zimbabwe played two one-day warm up matches against South African teams at the start of the One Day International series. Before the series began they played Northerns, losing by eight runs. After their first ODI against South Africa they played another match against Boland, winning by five wickets.Zimbabwe in South Africa 1999/00, CricketArchive. Retrieved 13 April 2018.

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