PIC: Thabang Monare of Orlando Pirates is challenged by Celimpilo Ngema of Marumo Gallants during the 2022 Nedbank Cup Last 16 clash

Twelve of the 16 sides left in the 2023 Nedbank Cup have been to this stage before, and while some have had mixed results, for others the Last 16 has been a round to be enjoyed with many happy memories.
For four clubs, this will be their debut and the dream of a quarterfinal place remains very much in touch. They are topflight Sekhukhune United, second-tier Casric Stars, and third-tier sides Dondol Stars and Mpheni Home Defenders.

We look at the Last 16 records of the remaining 12 teams to see how they have fared over the years.

AMAZULU

P7 W3 D1 L3 GF13 GA10
It is been a mixed bag for Usuthu at this stage of the competition with three wins and three defeats to go with a penalty shoot-out win against Moroka Swallows in 2010 on their way to the final, which they lost to BidVest Wits. Those victories came against second-tier sides Vasco da Gama (2008), Carara Kicks (2011) and Witbank Spurs (2012), but since then there have been losses to Wits (2014), Ubuntu Cape Town and Black Leopards (2021).   

CAPE TOWN SPURS

P4 W2 D2 L0 GF6 GA4
Spurs have rebranded from Ajax Cape Town, who were Nedbank Cup finalists in 2015. But the famous old club has only been to the second round of the competition on four occasions since 2008, a surprisingly low count. The good news for fans is that they have not lost outright in any of those games. They beat second-tier Nathi Lions (1-0) in 2009, but then lost on penalties to Free State Stars following a 1-1 draw in 2010. They edged Bloemfontein Celtic 1-0 on their way to the 2015 final, and drew 3-3 with Cape Town All Stars in 2021 after the teams had drawn 3-3.  

CHIPPA UNITED

P5 W3 D0 L2 GF7 GA5

Chippa are appearing in the Last 16 for the sixth time and have had mixed results at this stage. They beat Polokwane City 2-0 in 2017, but lost 2-1 to eventual champions Free State Stars in 2018. The following year they ousted second-tier Tshakhuma Tsha Madzivhadila with a 2-0 win. They lost 2-0 to BidVest Wits in 2020, but bounced back a year later to defeat Cape Town City 2-1. In three of the last four occasions when they have advance past the Last 16, they have reached the semifinals at least.

KAIZER CHIEFS

P12 W7 D2 L3 GF25 GA13

Chiefs have been a mixed bag in the Last 16, with all three of their outright losses coming to lower league opposition – University of Pretoria (2009), FC Cape Town (2010) and Black Leopards (2015). They also suffered penalty shoot-out defeats to Mamelodi Sundowns in 2008 and Highlands Park in 2020. This is the first time they have reached the Last 16 since that loss to Highlands three years ago.

LAMONTVILLE GOLDEN ARROWS
P7 W3 D0 L4 GF5 GA9
Golden Arrows lost three of their first four visits to the Last 16 since 2008, but have had a strong record since then. Defeats to Maritzburg United (2012) and Mamelodi Sundowns (2013, 2014) made for a disappointing run, before they broke their duck with a 1-0 vic tory over third-tier Natal United (2015). They lost to Baroka FC the following year, but then recorded a famous win over Sundowns (2017) and defeated Witbank Spurs on their last visit to the Last 16 in 2019.  

MAMELODI SUNDOWNS

P13 W10 D1 L2 GF29 GA7

Sundowns have largely had things their own way in this stage of the competition, having been knocked out just twice in their 12 fixtures. They have played Lamontville Golden Arrows three times in the Last 16, winning two of those, their one defeat coming in a 1-0 loss in 2017. Their only other exit at this stage of the competition was in 2009 at the hands of Platinum Stars. They did play to a 1-1 draw with Kaizer Chiefs the year before, but triumphed 5-4 on penalties. Last year they thumped third-tier Mathaithai 6-0. 

MARUMO GALLANTS

P3 W0 D2 L1 GF3 GA5

Gallants have been to the final in the last two editions of the Nedbank Cup but needed penalties to advance from this stage in the previous two seasons. They beat Swallows FC following a 2-2 draw in 2021 and then ousted another Soweto side at this stage in 2022 following a shoot-out win over Orlando Pirates after the sides drew 1-1. That was their third appearance at this stage after their debut in 2019, when they lost 2-0 to Chippa United. Gallants were known as TTM back then and were a second-tier side. 

ORLANDO PIRATES

P11 W6 D1 L4 GF22 GA11

Pirates have certainly not had it all their own way in this stage of the competition with four outright defeats and a penalty shoot-out loss to go with six wins. Those outright defeats were all by single-goal margins and came against Bloemfontein Celtic (2009), Free State Stars (2012), SuperSport United (2015) and Cape Town City (2018). They lost to Marumo Gallants last season on penalties after a 1-1 draw. By contrast, their victories have largely been emphatic, with wins over ALS Puk Tuwana (4-0), United FC (3-1), Santos (2-0), Jomo Cosmos (3-1), Free State Stars (4-1) and Maritzburg United (3-1). 

ROYAL AM

P2 W2 D0 L0 GF3 GA1

Royal AM have a 100% record at this stage of the competition from their two previous visits here. Their first was against then fellow Motsepe Foundation Championship side Mbombela United in 2020. They ended up winning 2-1 thanks to a late winner from Diego Brown but lost 4-0 to BidVest Wits in the quarterfinals. Once promoted to the topflight, they beat Swallows FC 1-0 last season.

STELLENBOSCH FC

P1 W0 D0 L1 GF1 GA2
Stellenbosch have only been to the Last 16 once before, back in 2018, when they lost 2-1 to away at Kaizer Chiefs. This is their sixth participation in the Nedbank Cup, so this is a statistic they will want to improve on in the coming years.    

TS GALAXY

P2 W1 D1 L0 GF2 GA1

Galaxy were famously Nedbank Cup winners in 2019 while still campaigning in the second-tier, and along the way met Jomo Cosmos in the Last 16. They advanced 1-0 thanks to an own goal from Dahou Lebahi. They reached this stage for the second time in 2022 and after a 1-1 draw with Baroka FC, were ousted on penalties.

VENDA FOOTBALL ACADEMY

P1 W0 D1 L0 GF3 GA3
Venda are making their second appearance in the Last 16 in as many years and will this time hope to advance. They came close in 2022 when they played to a 3-3 draw with fellow second-tier side University of Pretoria but lost in a penalty shoot-out.