"Andy Bichel stopped us winning a game at the 2003 World Cup in South Africa. Shane Bond had gone six-for-nothing but Andy batted with Michael Bevan and saved the match.
"I remember it vividly, so that was about trying to inflict some damage on him. It still didn't make me feel any better, though."
Fleming's disposition will markedly improve if the current Black Caps side can do something he never managed and win the World Cup. It will be especially sweet to see off Australia en route to victory and, based on the Harbour Bridge encounter, the early signs are promising.
Bichel conceded the home side emerged triumphant but he was satisfied just to be involved in such a unique location.
"Weirder places for cricket? No, that takes the cake," he said. "I've taken trophies to the top of bridges but to actually play a game was very special."
Fleming felt likewise and joked that the top of the bridge marked the loftiest heights of his career.
Bichel, Damien Fleming, Stephen Fleming and Chris Harris show off the Cup.
"It's not something I ever envisaged doing," he said. "To do it for a good reason - 100 days to go till the World Cup - it had real purpose."
Fleming, now coaching Indian Premier League side Chennai, will play a part promoting the tournament to the subcontinent, an area of expertise he has developed since joining the Super Kings in 2008. The 41-year-old is part of an export company that maximises his profile in India, while he has also teamed with Education New Zealand to raise awareness of this country as a study destination for a growing Indian middle class.
But Fleming will be a keen spectator when the World Cup kicks off on February 14, hoping to be as entertained as those crossing the Harbour Bridge who unwittingly drove past the latest chapter in a transtasman cricket rivalry.
"It was funny watching some of the drivers' expressions, trying to get to grips with what was going on," he said.
"You could almost feel their bewildered looks and imagine their conversations afterwards: 'I think I just saw a cricket game going on!' 'Yeah, righto, sweetheart'."