Road To The Crowns
A Century of History Behind South Africa’s Championship Paths
Above: Horse Chestnut storms to victory at Turffontein (image: JC Photographics)
With the 2026 Highveld Feature Season just a week away, Turffontein once again prepares to host two series of South Africa’s key three-year-old classics.
The journey begins next Saturday, 7 February with the Gr2 Gauteng Guineas and Wilgerbosdrift Gr2 Fillies Guineas over 1600m, the opening legs of the SA TAB Triple Crown and Wilgerbosdrift Triple Tiara. Attention then turns to Saturday, 7 March, when the Gr1 SA Classic and SA Fillies Classic over 1800m raise the bar, before the championship paths reach their ultimate tests on Saturday, 4 April in the Gr1 SA Derby and Gr2 SA Oaks over 2450m.
In 2026, a bonus of R2-million will be payable to the winner of the Triple Crown, with R1-million on offer to any filly who can win all three legs of the Triple Tiara.
The two series are modern in structure but rooted in long-established ideals, and they remain the clearest measure of class, progression and stamina among South Africa’s three-year-olds.
Each of these six races has its own history and identity, shaped over decades by changing programmes, venues and priorities, and together they charted the gradual evolution of what would eventually be recognised as South Africa’s Triple Crown and Triple Tiara.
Keep in mind that, for the most part of the 20th century, there were three Grade 1 races for three-year-old males all over 1600m – the Benoni Guineas at Gosforth Park, the Cape Guineas (at Milnerton and later at Kenilworth) and the SA Guineas at Greyville. The distance of the Benoni Guineas was increased to 1800m in 1982, when it was run as the Sigma Classic, and the contest eventually morphed into the Grade 1 SA Classic of today.
The inaugural winner of the Benoni Guineas in 1913 was a horse named Hailstorm, by Goring Heath.
In the early part of the 20th century, the Benoni Guineas (1600m) formed one leg of the original South African Triple Crown. In those days, the other two legs were the SA Derby (2400m) and Benoni St Leger (2700m).
The first three-year-old to sweep the SA Triple Crown was Colesberg (Wilfrid), who was also a high-class two-year-old and took the honours back in 1920. Remarkably, the South African Triple Crown was won for four consecutive years in the early 1920’s. Colesberg’s victory preceded those of Dignitary (Greatorex - 1921), Antonio (Pietri - 1922), and Red Ronald (Brown Ronald - 1923). This is a staggering occurrence, and one which has happened but rarely throughout the world.
Above: South African legend, Lenin
One of the race’s greatest ever winners, and a true South African legend, was Lenin (Sunstone), who was victorious in 1940. Lenin outclassed his rivals in the Guineas, winning by 10 lengths. An established champion prior to the race, Lenin went on to win the S A Derby by six lengths, and was awarded the Summer Handicap on disqualification of the original winner, Spanish Armada.
Lenin won 18 races during his career and was a famous weight carrier. The champion won from 1000-3200 metres under various heavy weights, and once carried as much as 76 kgs.
Above: The great Hawaii (photo: supplied)
Arguably the most important horse ever to win the then Benoni Guineas was the great Hawaii (Utrillo II), who took the 1967 renewal for George Azzie and Raymond Rhodes. Not only was Hawaii a champion here and in the USA, he has left a real stamp on the breed mainly through his daughters. He did sire an Epsom Derby winner in 1980 victor Henbit, as well as 1978 runner-up Hawaiian Sound and third-placed Hunza Dancer in 1975.
Other notable winners were Yataghan (Marsolve - 1972), Wagga Wagga (New South Wales - 1977) and Quarrytown (Silver God - (1979), while Nic van Tonder’s Port Pegasus (Trocadero) won the last 1600m renewal in 1980 under jockey Michael Coetzee.
4Racing’s Robert Garner, who was Racing Editor of The Star from 1975 to 2001, and later worked as Marketing and Communications Manager for Phumelela, said that a decision was made in 1982 to change the distance of the Benoni Guineas to 1800m, and the name of the race changed to the Sigma Classic with different sponsors over the next several years.
Garner explained: “In a huge stride forward for SA racing, the distance of the race was increased to 1800m in 1982. In the same year the race was moved to autumn from its traditional time slot towards the end of the year. Until the distance was increased, the three principal races for three-year-olds in South Africa had all been run at 1600m, which was illogical in light of the country’s major races for older horses being decided over 2000m and 2200m. Proper middle-distance classics were critical and the now SA Classic was the first followed later by the Daily News 2000.
“In the 1990s the SA Classic alternated between Gosforth Park and Turffontein for several years. In 1999 the race was returned to its traditional venue at Gosforth Park, but Turffontein later became its permanent home after the East Rand racecourse was closed and sold.”
THE SA CLASSIC
The ‘Sigma Classic’ was run over 1800m on 6 March 1982 and won by David Payne’s stunning grey filly Breyani (Jamaico), who took on the colts at Gosforth Park and reigned supreme for jockey Robbie Sham.
The race was run as the ‘Administrator’s Classic with winners like Bodrum (Free Ride 1984), and became the ‘Southern Sun Classic’ in 1985, won by Herman Brown’s Yamani (Elevation).
The formidable filly Roland’s Song (Roland Gardens) won the 1989 and last renewal of the Southern Sun Classic, before the name was changed again to ‘Administrator’s Classic’ and won by more stars including Empress Club (Farnesio – 1992), National Emblem (National Assembly – 1995) and London News (Bush Telegraph – 1996).
THE GAUTENG GUINEAS
With the 1800m Classic firmly established, the racing clubs in the old Transvaal re-instituted a Guineas over 1600m, and it was named the Listed Newmarket Guineas. It was staged at the old Alberton track for the first time in February 1988 and was won by Cliffie Otto-trained Duzzn’t Stop (Royal Prerogative), ridden by Dickie Roberts.
In April 1993 the race was upgraded to Grade 3 status and re-named, the MEC Guineas, the inaugural contest going to Young Victor (Lucy’s Axe) for Spike Lerena and Weichong Marwing.
The MEC Guineas later reverted back to the Newmarket Guineas and was upgraded again in 1999, when it received Grade 2 status and served as an optional first leg of the inaugural, re-arranged SA Triple Crown, alongside the Grade 1 Cape Guineas (an arrangement which was discontinued in 2021). The series was completed by the Grade 1 SA Classic and Grade 1 SA Derby.
The first Grade 2 Guineas was won by Fort Defiance (Fort Wood), although his talent was overshadowed in the 1998/99 season by his exceptional stablemate Horse Chestnut (Fort Wood). Horse Chestnut had already captured the Grade 1 Cape Argus Guineas, before adding the SA Classic (then still run at Gosforth Park) and the SA Derby at Turffontein — three Grade 1 victories at three different venues, and a sequence that laid the foundation for the modern Triple Crown, in spectacular fashion.
Fifteen years elapsed before the next SA Triple Crown winner, Louis The King (Black Minnaloushe), emerged in 2014. With Gosforth Park (2000) and Newmarket (2004) both closed, Geoff Woodruff’s colt won the Grade 2 Gauteng Guineas, the Grade 1 SA Classic and the Grade 1 SA Derby all at Turffontein, ridden by Robbie Fradd.
Michael Azzie’s Abashiri (Go Deputy) achieved the feat again in 2016 under regular jock Karl Zechner, and Luke Ferraris won the Triple Crown as an apprentice on Malmoos (Captain Al) in 2021.
THE GAUTENG FILLIES GUINEAS
The Grade 1 Fillies Guineas was run as ‘The Stuttafords Cup’ in December 1981, a race that started a sequence of Graded wins for Breyani. The race was sponsored by Mike’s Kitchen in 1986 and then reverted to the Grade 1 Gosforth Park Guineas and later the Grade 1 Bloodline Fillies Guineas. Winners included Enchanted Garden (Roland Gardens – 1985), and Mystery Guest (Northern Guest – 1989) who bolted and ran around the entire track at the start, but still raced home first after being reloaded.
The race was downgraded to Grade 2 in 1992, but still drew the best fillies in the land, including winners like Spook Express (Comic Blush – 1998), Promisefrommyheart (Elliodor, 2000) and Zirconeum (Jallad – 2009).
THE SA FILLIES CLASSIC
In 1999, the Racing Association and Highveld owner-trainer St John Gray were instrumental in a move to introduce a fillies’ equivalent to the SA Triple Crown and so was born the SA Triple Tiara, which led to the 2000m SA Oaks Trial being transformed into the Grade 1 SA Fillies Classic as the Triple Tiara’s equivalent second leg to the SA Classic – to follow the Grade 2 and renamed Gauteng Fillies Guineas with the Grade 2 SA Oaks forming the last leg of the fillies’ series. The inaugural winner of the first Triple Tiara Gauteng Fillies Guineas was Sean Tarry’s Golden Apple (Northern Guest) in 1999, but the series was only won for the first time in 2011 by Mike de Kock’s sensational filly, Igugu (Galileo).
Above: The Oppenheimer family have won the Triple Tiara twice (image: JC Photographics)
Wilgerbosdrift picked up sponsorship of the Triple Tiara in 2013, when the series was again won, this time by the Bridget Oppenheimer-owned Cherry On The Top (Tiger Ridge), for which trainer Ormond Ferraris kept Nooresh Juglall on board for all three legs.
The Oppenheimer family (Jessica Jell: Mauritzfontein) won the series again in 2020 with Cherry On The Top’s close relation, Summer Pudding (Silvano), trained by Paul Peter, starting a sequence of three successive Triple Tiara heroines.
Paul Matchett-trained War Of Athena (Act Of War), won the 2021 series for jockey Muzi Yeni and Sean Tarry landed the spoils in 2002 with Rain In Holland (Duke Of Marmalade), a first series win for himself, Drakenstein Stud and Richard Fourie.
THE SA DERBY
The race was first run in Port Elizabeth in 1885 before relocating to Turffontein at the turn of the century by which time Johannesburg had become the racing centre of South Africa in the wake of the wealth generated following the discovery of gold. The distance has remained unchanged, barring a slight increase from 2413m to 2450m in 1970. It was shifted from December to its current April slot in 1971 and has evolved into one of Africa's most prestigious racing events.
Victory in the 1907 Derby went to the filly Diana (Uniform), who highlighted the prominent role of British sires in shaping early South African bloodstock. Other famous early winners included Moonlit (Cross Bow - 1935), who went on to win the Cape Met twice; Lenin (Sunstone -1940), as referred to above; Tiger Fish (Janus – 1957), who also won the Durban July; Riboville (Prince Ribot – 1973), another Durban July winner later in his career); Super Quality (Elliodor – 1996), also a July victor; international stars Horse Chestnut (Fort Wood – 1999), Grey’s Inn (Zabeel – 2004) and Irish Flame (Dynasty – 2010).
The Derby, like in the UK, is also a perennial producer of top stallions, including from the modern era Riboville, Horse Chestnut, Grey’s Inn and Irish Flame above, and others like Elevation (High Veldt – 1972); Elusive Fort (Fort Wood – 2006), Pomodoro (Jet Master – 2012) and recently to stud, Malmoos (Captain Al, 2021).
The Derby attained Group 1 status as part of South Africa's adoption of international grading standards in the late 20th century, a development that occurred alongside the formalization of merit rating systems and global racing classifications beginning in the 1970s.
THE SA OAKS
The South African Oaks over 2450m is the oldest and most demanding classic race for three-year-old fillies in the country. It is naturally rich in history and fascinating statistics, but due to decades of incomplete record-keeping, those are still in the process of being assembled, checked and edited.
The first SA Oaks was won in 1914 by a filly named Pendant (by Sidus), trained by Fred Murray and ridden by William Watson. Murray was a trainer of some repute – the only one so far to have won four successive Durban July Handicaps (1910-1913).
The 1916 Oaks produced a memorable winner in Opera Cloak, a filly bred by AE Passmore by St Maurice out of Pellerine. The same mating had produced Passmore’s 1912 SA Derby winner, Van Raalte.
Opera Cloak was a diminutive filly, so much so that she was eligible for Galloway races. Accordingly, ‘AE’ chose to keep and race her for his own account and trained her himself. After a good win in a Flying Handicap at the Johannesburg Turf Club on 23 December 1916, ‘AE’ entered her for the Oaks, to be run over a mile and a half on 30 December.
While it is fairly remarkable for a mare to produce full siblings who both go on to be classic winners, the story gets more remarkable still. ‘AE’, who was in his fifties by now, held a gentleman rider’s license and in what must be a world record, AE is down in the history books as the breeder, owner, trainer AND rider of the 1916 Oaks winner, beating in the process, Ike Strydom, the champion jockey of his day.
The Oppenheimer family have a phenomenal Oaks record. They first won it in 1962 with Dame de Coeur (Janus – No Deal) – from two other Mauritzfontein-breds, Pafuri and The Widow. They won it again in 1963 with Baccarat, a full sister to Dame de Coeur, and have won it a total of 14 times to date.
Mauritzfontein’s classic stallion Free Ride (Timeform 129) bred five SA Oaks winners – Angelina, Free Style (SA and Natal Oaks), Murena (winner of the 1972 SA Oaks beating Switched On and Hula Queen, all Mauritzfontein-bred and all by Free Ride), Vicereine, Grease Paint (out of SA Oaks winner Julie Andrews by Shantung); and Free Ride also bred Natal Oaks winner With Pleasure (out of Willingly by Wilwyn) as well as Bodrum and Principal Boy.
Above: Ormond Ferraris with Pretty Border (image: supplied)
South African Hall-Of-Famer, Ormond Ferraris, trained a record eight Oaks winners, starting with Pretty Border (Herbaceous – 1976) and concluding with Cherry On The Top in 2013.
In the last fifty years, Piere Strydom and Anthony Delpech share the most Oaks wins – four apiece – while Richard Fourie has won three of the last five renewals, including last year’s race on Joe Soma’s Fiery Pegasus (Fire Away).
Sources:
www.aro.co.za
The Sporting Post: A Classic History, March 2012.
AE’s World Record: Robyn Louw, Sporting Post, July 2016
The Meaning Of Mauritzfontein: Robyn Louw, Sporting Post, July 2017
Grokopedia: South African Derby
Hollywoodbets Durban July: Roll Of Honour