Nedbank Cup: Listing 5 of the Biggest Cup Upsets Ahead of Mamelodi Sundowns vs NB La Masia

• The first Nedbank Cup match kicks off at Dobsonville Stadium featuring a one-sided clash
• Dominant continental force, Mamelodi Sundowns will play a team one tier below them
• Hosts NB La Masia will hope that their two Orlando Pirates legends bring them luck

In South Africa's only inter-division cup competition, expectation and underestimation can be a deadly combo.

The opening fixtures of a cup competition can be tricky territory as the underdogs have little to lose in their one-off shot at the big names.

South African football regularly delivers surprises and Sports Brief looks back at the biggest cup shocks of the last 15 years.

Biggest Nedbank Cup upsets

1. Kaizer Chiefs vs University of Pretoria

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The big teams are always tipped to rack up the goals and sometimes forget about their defensive obligations. Amakhosi put three past a second-tier AmaTuks in 2009 but the Pretoria boys kept coming.

Goals from Mthokozisi Yende, Phenyo Mongalo and Thabo Moleko had Tuks ahead with 20 minutes to play. Siphiwe Tshabalala looked to have spared Chiefs' blushes with an 82nd-minute equaliser from the spot, adding to goals from Josta Dladla and Jose Torrealba.

Tuks had been reduced to 10 men following the penalty, but it did not deter them, as Mongalo went back to the other end four minutes later to beat Itumeleng Khune for the fourth time that afternoon.

2. Platinum Stars vs Als Puk Tawana

A story of two teams that no longer exist. Platinum Stars were dissolved and moved to Cape Town in 2018, while the then-third division club have since ceased operations.

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Stars were a midtable PSL team in 2010 but would go on to finish second in the league two years later and win the Telkom Knockout and MTN8 in 2013.

The students from North-West University were never behind that day, taking a 2-0 lead into halftime before Jabulani Shongwe made it 3-1. Kagiso Senamela made it 3-2 but Tawana held on for a win set in North-West lore.

3. Orlando Pirates vs Maluti FET College FC

Lucky Mokoena and Mashale Rantabane will forever remember the day when third-tier students from the Free State humbled Soweto's mighty skull and bones in 2013.

The pair scored twice each as Maluti FET trounced Orlando Pirates 4-1. The students were ahead from the 47th second of the match with only Oupa Manyisa able to net for the Buccaneers.

It was a season to remember for Maluti FET, as they were promoted to the National First Division that season, as per Supersport.

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4. Cape Town City vs Acornbush United

Few names scream part-time giant killers quite like 'Acornbush United'. Additionally, the most rewarding upsets involve holding onto the lead for more than 45 minutes.

That season's Telkom Knockout winners, Cape Town City, had only just recently purchased and rebranded Mpumalanga Black Aces when they came up against an aptly situated foe in 2017.

Playing in the heartland of the club they had just annexed, the home crowd were delirious as Mduduzi Nkosi's 42nd minute was enough to send City packing with their eardrums ringing.

5. Kaizer Chiefs vs TS Galaxy

Upsets don't come any sweeter than when accomplished in a cup final. When TS Galaxy were still moving up the ranks, they became the first, and to date, only NFD team to win the Nedbank Cup in 2019.

Amakhosi were approaching five years without a trophy and would have been odds on to return to the podium.

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The match looked set for extra time but Galaxy were awarded a 90th-minute penalty. Up stepped a 21-year-old Zakhele Lepasa to score against his future rivals.

NB La Masia CEO on Sundowns tie

Sports Brief recently reported on NB La Masia CEO, Rashid Toffie, commenting on their Nedbank Cup draw.

The National First Division club have been drawn against undefeated league leaders Mamelodi Sundowns.

The club are coached by Orlando Pirates legends Daine 'Lucky Charm' Klate and Moeneeb 'Slimkat' Josephs.