Striker Gustavo Paez struck either side of the break at James Motlatsi Stadium to set up the showdown with Ea Lla Koto, who earlier edged Platinum Stars 1-0 in Orkney.
The final of the one-day spectacle starts at 16h00.
Paez opened the scoring 18 minutes in, slotting home after being teed up by strike partner Bernard Parker.
The Venezuelan came close again shortly before the interval but was denied by a fine stop from goalkeeper Keeagile Kgosipula.
Chiefs threatened once more around the hour mark, as midfielder Hendrick Ekstein had a low shot saved following good work by experienced left-back Tsepo Masilela.
Parker also tried his luck in the latter stages as he steered a free-kick straight at Kgosipula following a foul on substitute Khotso Malope, who came on moments earlier for new signing Bhongolwethu Jayiya.
Paez, however, completed his brace from the spot in the 82nd minute, following a foul on Masilela in the area, to seal the result.
The Glamour Boys, who showcased Zimbabwean recruit Teenage Hadebe, will face Rollers again on July 22 at Francistown Stadium (15h00 kick-off).
Amakhosi will then close out their pre-season campaign with the Carling Black Label Cup clash with Orlando Pirates at FNB Stadium on July 19 (15h00 kick-off).
Chiefs: Khune (C), Mphahlele, Mathoho, Hadebe, Masilela (Khumalo 89'), Maluleka, Katsande, Ekstein, Jayiya (Malope 72'), Parker (Chirambadare 85'), Páez.
Unused subs: Bvuma, Sixhaso, Peterson, Katsvairo, Ngezana, Ngcobo S, Ngcobo.