Although Milford suffered a 2-0 defeat in that opening encounter, Pupuma was encouraged by the way his players stood up against the reigning champions.
Since then, the newcomers have put together an impressive record, winning three, drawing two and losing two of their seven league matches to collect 11 points and move into fifth place on the standings.
After Sunday’s emphatic 5-1 victory over neighbours Richards Bay, Pupuma credited the strong bond within his squad for helping Milford adjust to life in the Premiership.
"The first game against Pirates gave us the confidence and the belief that we can compete in this division. We gave the defending champions a few headaches on that day.
"Fortunately for me, these boys have been playing alongside one another for a long time and they would do anything for each other."
Pupuma has largely stuck with the squad that helped Milford secure promotion, making only a few additions rather than making wholesale changes to his playing personnel.
He believes retaining that core has helped the players adapt to the demands of the Premiership, while the club’s Diski Challenge side is also being viewed as a pathway for developing further senior reinforcements.
Pupuma remains unhappy that Milford and Richards Bay had to stage their first top-flight derby in Durban instead of playing at the uMhlathuze Sports Complex in Richards Bay.
The stadium was placed under a four-week PSL suspension following an inspection, forcing both clubs to relocate their home fixtures during that period.
Sunday’s derby was consequently played at the Sugar Ray Xulu Stadium and Pupuma believes the occasion would have attracted a much bigger crowd had the match been played in Richards Bay.
"No I'm not happy because if we were in Richards Bay we were going to have 8,000 fans attending. We don't have the facilities and means to bring them to certain games like Richards Bay did."
Pupuma believes the depth available to him, together with the work being done at training, will enable Milford to maintain their performance levels over the course of the season.