Whitfield made 33 off 25 balls at five, an innings replete with deft cut shots and drives.
Taewa won the coin toss and opted to bat against The Admiralty.
First man in Patrick McInnes - averaging 44 for GBHS Second XI in the Poverty Bay Senior B T20 competition - set an aggressive tone by hitting four boundaries in his 11-ball knock of 22.
Taewa and No 4 Arthur Cave (8) had a partnership of 45 before The Blues and Royals were dismissed for 99 in the 14th over, Raffaele Colucci picking up two wickets for The Admiralty.
Mahabalage was the mainstay of The Admiralty batting response before he was caught off promising opening bowler Tarn Boyle (1-22 off 3).
His team were all out for 90 in the 16th over.
“Today’s game was a good one and I liked the start that we made, but we still need to bat for the full 20 overs,” Taewa said. “Bowling-wise, we put them under pressure, then knocked them over.”
Jonah Reynolds won the toss in the King’s Own-Life Guards’ stoush and his younger brother Harvey outshone all other run-scorers on the day with 65 not out off 48 balls in a team total of 144-5.
The Life Guards were dismissed for 96 in the 18th over.
Harvey and Jonah are now regular first-team players for the OBR Premier team.
The ability of players to step up from the Junior Colts to Challenge Cup cricket, and even from Challenge Cup competition to Premier Grade play, confirms the value of a step without retirements or grace periods for batsmen.
“We lost but I’m happy with my bowlers’ performance, and with how well Jack Williams [16 at No 7] timed the ball when he batted. He was really positive,” Whitfield said.
“In terms of my own innings, it was good to spend time at the crease. Hopefully that translates into more runs for the Boys’ High seconds.”