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1 March 2014 

George Campbell vs. KZN Development
Pinetown vs. Port Natal

8 March 2014 

Port Natal vs. George Campbell
Durban High School vs. KZN Development

11 March 2014

George Campbell vs. Pinetown

15 March 2014 

Westville Boys' High vs. Glenwood
Kearsney College vs. Northwood
Hillcrest vs. George Campbell
Port Shepstone vs. Clifton
Port Natal vs. Durban High School

18 March 2014 

Durban High School vs. George Campbell

22 March 2014

Glenwood vs. Michaelhouse
St. Charles College vs. Hilton College
Maritzburg College vs. Northwood
Kearsney College vs. Westville Boys' High

29 March 2014 

Westville Boys' High vs. Marlow Landbou
Glenwood vs. Diocesan College
Durban High School vs. Pretoria Boys' High
Michaelhouse vs. Queen's College
Kearsney College vs. Grey Boys' High School

31 March 2014 

Kearsney College vs. Pretoria Boys' High
Michaelhouse vs. Graeme College
Durban High School vs. King Edward VII
Westville Boys' High vs. Queen's College
Glenwood vs. Jeppe Boys' High 

2 April 2014 

Westville Boys' High vs. Jeppe Boys' High 
Michaelhouse vs. Grey Boys' High School
Durban High School vs. SACS

9 April 2014 

Durban High School vs. Clifton

12 April 2014 

Voortrekker (Pietermaritzburg) vs. Glenwood
Maritzburg College vs. Pretoria Boys' High
Westville Boys' High vs. Durban High School
Northwood vs. George Campbell
Clifton vs. Port Natal 

17 April 2014 

Kearsney College vs. HTS Middelburg
Westville Boys' High vs. Nico Malan 
Glenwood vs. Dale College 
Northwood vs. Graeme College

19 April 2014

Kearsney College vs. Dale College
Glenwood vs. EG Jansen
Westville Boys' High vs. Grey College 
Northwood vs. Menlopark

21 April 2014 

Glenwood vs. Framesby
Westville Boys' High vs. Selborne College
Kearsney College vs. EG Jansen
Northwood vs. King Edward VII

26 April 2014 

Westville Boys' High vs. Michaelhouse
Hilton College vs. Kearsney College
Northwood vs. Jeppe Boys' High
Durban High School vs. Parktown Boys' High
Clifton vs. St. Charles College

28 April 2014 

Glenwood vs. Waterkloof (Wildeklawer)
Maritzburg College vs. Monument (Wildeklawer)

29 April 2014 

St. Charles College vs. George Campbell

30 April 2014 

Maritzburg College vs. Diamantveld (Wildeklawer)
Glenwood vs. Outeniqua (Wildeklawer)

3 May 2014 

Michaelhouse vs. Hilton College
Kearsney College vs. St. Charles College 

10 May 2014 

Durban High School vs. Glenwood
Maritzburg College vs. King Edward VII
Westville Boys' High vs. Pretoria Boys' High
St. Charles College vs. Michaelhouse
Northwood vs. Hilton College
Kearsney College vs. George Campbell
Voortrekker (Pietermaritzburg) vs. Port Natal
Clifton vs. Kearsney College II

17 May 2014 

Glenwood vs. George Campbell
Maritzburg College vs. Kearsney College
Westville Boys' High vs. Empangeni
Northwood vs. Michaelhouse
Hilton College vs. Durban High School
Port Natal vs. Glenwood II
Clifton vs. Pinetown
Voortrekker (Pietermaritzburg) vs. St. Charles College

20 May 2014 

Durban High School vs. Michaelhouse

24 May 2014 

Glenwood vs. Maritzburg College
Westville Boys' High vs. King Edward VII
Northwood vs. Durban High School
Voortrekker (Pietermaritzburg) vs. George Campbell
Richardsbaai vs. Port Natal
Clifton vs. St. Andrews (Bloemfontein)

31 May 2014 

Maritzburg College vs. Hilton College
Glenwood vs. Monument
Michaelhouse vs. St. John's College
Kearsney College vs. St. Stithian's College
Port Natal vs. Northwood
George Campbell vs. Clifton
Durban High School vs. St. Charles College 

7 June 2014 

Hilton College vs. Glenwood
Michaelhouse vs. Maritzburg College
Port Natal vs. Westville Boys' High
Durban High School vs. Kearsney College
Northwood vs. St. Charles College
George Campbell vs. Empangeni/Richardsbaai
Port Natal vs. Westville Boys' High II
Clifton vs. Treverton

14 June 2014 

Glenwood vs. Northwood
Maritzburg College vs. Durban High School
Hilton College vs. Westville Boys' High
Kearsney College vs. Michaelhouse
Clifton vs. St. Charles College 

21 June 2014 

Glenwood vs. Kearsney College 
Westville Boys' High vs. Maritzburg College
Michaelhouse vs. St. Charles College
George Campbell vs. Hilton College
Port Natal vs. Hilton College II
Voortrekker (Pietermaritzburg) vs. Clifton

28 June 2014 

Hilton College vs. Michaelhouse

26 July 2014 

Glenwood vs. Grey College
Maritzburg College vs. Affies

2 August 2014 

Glenwood vs. Affies
Maritzburg College vs. Pretoria Boys' High 

9 August 2014 

Maritzburg College vs. Glenwood

16 August 2014 

Glenwood vs. KZN Development
Maritzburg College vs. Grey College