Upington City v Durban City

Upington City welcome Durban City to Mxolisi Dicky Jacobs Stadium on Saturday (15h00).
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Established just recently in 2021, Upington City quickly became a force in the ABC Motsepe League (third tier), winning the 2022/23 Northern Cape stream title and gaining promotion to the Motsepe Foundation Championship (second tier) for the 2023/24 season.

Upington made headlines by upsetting Magesi (5-4) on penalties in the Round of 32 after the match ended 0-0. Ninth in the Motsepe Foundation Championship, Upington are strong on their own turf with just two losses at home this season across all competitions.

Meanwhile, Durban City advanced from the Round of 32 (3-2 on penalties) over Chippa United after the match ended 0-0. City have exceeded expectations in their debut season in the Betway Premiership as they are sixth on the Betway Premiership standings. Key to their success is their defensive solidity, having conceded just 13 goals from their 18 matches played.

There is however, a cloud of uncertainty over the KZN outfit as the club are under the mentorship of a new manager - Alan Freese - after the shock departure of Sinethemba Badela.

The sides met twice in the second-tier of South African football last season and the Durbanites came out on top on both occasions (3-1 and 1-0). History favours Durban City, but Cup knockout ties often produce surprises - especially when both teams have familiarity from league battles.

Golden Arrows v Stellenbosch FC

Stellenbosch FC travel to Durban this Saturday to face Lamontville Golden Arrows in a highly anticipated Nedbank Cup Round of 16 clash at King Zwelithini Stadium (18h00).

Both sides are managed by experienced coaches - Gavin Hunt at Stellenbosch and Manqoba Mngqithi at Arrows - making this a tactical duel as much as a contest of players.

The Maroons have been in strong cup form, having reached the quarter-finals in each of the last three seasons and finishing runners-up to Orlando Pirates in the MTN8 earlier this term. They also defeated Kaizer Chiefs at home in the previous round, while Arrows recorded a convincing 3-0 win over Orbit College after weather forced a rescheduling.

Arrows are ninth in the Betway Premiership standings with 20 points from 17 matches and are coming off the back of a 2-0 win over Magesi in their last fixture played on August 13.

Meanwhile, Stellies are not far behind in 13th with 16 points from 16 matches and drew 1-1 with Magesi on Wednesday evening, meaning Arrows would have had far more rest than Gavin Hunt's side.

The league meetings this season have been entertaining, with Stellenbosch edging Arrows 4-3 in a thriller, and historically the Winelands club have dominated the head-to-head, winning six of the last 13 encounters, including two wins and four draws in Durban.

With both sides closely matched in the Premiership standings, the cup offers a chance to secure silverware and potential CAF Confederation Cup qualification. Hunt has instilled renewed energy in his squad, while Mngqithi hopes home advantage will help Arrows overcome a revitalised Stellenbosch. Fans can expect a high-intensity clash where experience, tactical acumen, and individual brilliance will likely decide which side progresses to the quarter-finals.

Milford FC v Mkhambathi FC

Milford FC host Mkhambathi FC at Richards Bay Stadium in a KZN derby on Sunday (15h00).

Motsepe Foundation leaders Milford are flying high in the second-tier and are strong at on their own patch where they have been rarely beaten this season. Xanti Pupuma is chairman-manager of the side and oversaw their penalty shootout victory over Soweto Super United in the Round of 32.

Milford have tasted success in the Nedbank Cup before as they knocked Kaizer Chiefs out of the Round of 32 in the 2023/2024 season and will be looking to go one further this time around as they attempt to make the quarterfinals.

Mkhambathi, also from KZN, play in the ABC Motsepe League in the province and are debutants in the competition. Adding to the strong KZN presence in the last 16, Mkhambathi beat Lerumo Lions 2-1 in the Round of 32 encounter.

They're one of the few amateur/regional teams to reach this stage, joining the likes of Jacksa Spears in impressing at national level this season.

This will be the first confirmed meeting between the sides and provincial bragging rights are on the line.

Jacksa Spears v Vasco da Gama

Jacksa Spears will host fellow ABC Motsepe League side Vasco da Gama at Sukuzi Stadium in Kimberley on Sunday (15h00).

Jacksa Spears compete in the ABC Motsepe League (third tier) of South African football, representing the Northern Cape province. They have competed in the Nedbank Cup before - that was in 2013, when they reached the Last 32 before bowing out.

The club is coached by James Mothibi, a former professional player who returned to guide Spears alongside Bongani Cashibe, bringing valuable experience to the team's tactical approach.

Spears reached the Nedbank Cup Last 16 by beating FC Cardinals 4-2 after extra time, coming from behind in a dramatic tie. This run marks a rare deep Cup showing for a third-tier side.

Vasco da Gama (Cape Town) also compete in the ABC Motsepe League (third tier) after previously featuring in higher divisions including a season in the top-flight in the 2010/2011 season. In 2015, they reached the semifinals of the Nedbank Cup before losing to eventual winners Mamelodi Sundowns while they also participated in the 2011 and 2013 editions.

Vasco reached the Last 32 after qualifying through their provincial competition, then beat Western Cape side Luthuli Brigades 4-1 to reach this Last 16 tie.

In the 2024/25 Nedbank Cup, Vasco suffered a heavy 7-0 defeat to TS Galaxy in the Last 32 - a result that highlighted the gulf to higher divisions but also provided valuable experience.

It will be the first meeting between the sides.

University of Pretoria v Sekhukhune United

Sekhukhune United will be looking to avoid an upset when they travel to face University of Pretoria FC (amaTuks) at Tuks stadium on Sunday (15h00).

AmaTuks are 11th in the Motsepe Foundation Championship and have a notable history in the Nedbank Cup that stretches back over a decade. Their most famous run was in 2009, when, as a second-tier side, they reached the Nedbank Cup final, eventually losing 1-0 to Moroka Swallows at the Rand Stadium.

In 2010 they reached the quarterfinals, and in 2015 and 2016 they made it to at least the Last 16, including a dramatic 3-3 tie with SuperSport United in 2016, which they lost on penalties. AmaTuks also advanced to the quarterfinals of the 2023-24 Nedbank Cup, famously defeating Premiership side Moroka Swallows 2-1 to book a place in the last eight before being ousted by Mamelodi Sundowns on penalties.

Sekhukhune United are third in the Betway Premiership - now a consistent top-six side in the top-flight - and narrowly edged second-tier side Highbury FC 1-0 in the Round of 32. Babina Noko were runners-up in the 2022-23 Nedbank Cup, losing narrowly in the final to Orlando Pirates (1-2).

Eric Tinkler's men have lost just two of their last eight Betway Premiership fixtures - with those losses coming against Mamelodi Sundowns and Stellenbosch. With the fight for a top-three league finish more intense than ever, the cup presents Sekhukhune with an alternative path to qualify for continental football next season. Meanwhile, Kaizer Chiefs are showing signs of revival and pushing hard in the race for CAF qualification, making a strong cup run potentially crucial for the men from Limpopo.

New Stellenbosch striker Cheswyn Philander aiming for a regular starting spot