The result saw the Cape Winelands outfit inflict further cup heartbreak on Amakhosi, having already eliminated them from the Carling Knockout earlier in the season.
The win also provided a timely response for coach Gavin Hunt’s side after their recent CAF Confederation Cup defeat to CR Belouizdad, while ending Chiefs’ four-match winning streak in 2026.
Chiefs made several changes to their starting line-up following their recent victory over Zesco United, with Given Msimango, Paseka Mako, Thabiso Monyane, Thulani Mabaso, Mduduzi Shabalala and Gaston Sirino all brought into the side. Stellenbosch also shuffled their pack, recalling Thabo Moloisane and handing Devin Titus a starting berth.
The hosts made the perfect start, taking the lead after just 10 minutes. Flavio da Silva fouled Moloisane inside the box, leaving Nigerian midfielder Ibraheem Jabaar to confidently convert from the penalty spot past goalkeeper Brandon Petersen. Moloisane was forced off shortly afterwards after sustaining a facial injury during the incident.
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Stellenbosch doubled their advantage midway through the first half when Titus capitalised on loose possession on the edge of the area before unleashing a powerful strike into the top corner.
Chiefs dominated possession as they searched for a response before the break but were repeatedly frustrated by an inspired display from goalkeeper Sage Stephens. The shot-stopper denied Shabalala on multiple occasions and also kept out efforts from Sirino, Mabaso and Da Silva to ensure Stellies held a two-goal lead at halftime.
Amakhosi coach made attacking changes at the start of the second half, introducing Lebohang Maboe and Glody Lilepo, and the latter nearly made an instant impact when his snap shot rattled the woodwork shortly after the restart.
Chiefs were eventually handed a lifeline in the 56th minute when Da Silva converted from the penalty spot after a handball in the box, reducing the deficit and setting up a tense finale.
Despite the pressure, Stellenbosch remained dangerous on the counter-attack. Langelihle Phili came close to restoring the two-goal cushion but was denied by Petersen in a one-on-one opportunity, while Wonderboy Makhubu also squandered a late chance after being thwarted by the Chiefs goalkeeper in stoppage time.
Chiefs threw numbers forward in the closing stages in search of an equaliser but were unable to break down a disciplined Stellenbosch defence, as Hunt’s side secured their place in the last 16.
The defeat leaves Chiefs with only the Betway Premiership and CAF Confederation Cup still to contest this season, while Stellenbosch continue their pursuit of domestic silverware.