Fleming became New Zealand's most successful captain in September 2000 with a victory over Zimbabwe. This was the 12th win under his captaincy overtaking Geoff Howarth. Fleming was regarded by some as an underperformer with the bat, with one of the worst 50 to 100 conversion ratios in world cricket. However, since the 2003 tour of Sri Lanka, Fleming started to gain form, with 274 not out against Sri Lanka – when he declared rather than staying to reach 300 which would have been a record in New Zealand cricket history.