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West Indian Pooran smashed 62 off 34 balls as the Superchargers reeled in 147 to ensure Flintoff, who has been linked with the vacant England white-ball head-coach job after Matthew Mott's departure, got off the mark following defeat to Trent Rockets in his first game in charge.
England batter Harry Brook, captaining the Superchargers on his return from international duty, also weighed in with an unbeaten 34 off 20 balls - including a six to finish - to get his side home with 15 deliveries to spare.
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Southern Brave were not quite at their domineering best, as they had been at Utilita Bowl last week, but they did not do much wrong other than come up against Pooran with the bat and Adil Rashid with the ball.
On a track where spin was always going to be important, Rashid's one for 19 contributed to Brave's total of 146 for eight coming up perhaps a touch light - though it did still require the Superchargers' second-highest chase in the competition - but at the interval James Vince and his side would have felt in the game.
Jofra Archer fired up and touched 93mph but from the 15th ball onwards it was the Pooran show, the left-hander blasting five sixes and sharing a 50-run stand with Brook.
Player of the match - Nicholas Pooran
"It feels amazing," Pooran said. "After that first game we lost, playing back-to-back games here at home, we wanted the win.
"The guys played brilliantly, and I think the bowlers did amazingly. It's always beautiful to play here in England. The surface, the atmosphere - it's lovely."
What's next?
The Hundred continues on Wednesday with two more big games coming your way. Trent Rockets Women face Birmingham Phoenix Women at 3pm, before Trent Rockets host Birmingham Phoenix at 6.35pm.
Sky Sports will show all 68 games in The Hundred live, while you can also watch selected matches via free streams on Sky Sports' digital platforms and the Sky Sports Cricket YouTube channel.