1st Round
09.11.2013	Old Wykehamists		H - W		Old Wellingburians
09.11.2013	Old Haileyburians		5 - 1		Old Haberdashers
02.11.2013	Old Reptonians		3 - 2		Old Harrovians
02.11.2013	Old Malvernians		H - W		Old Wellingtonians
02.11.2013	KCS Old Boys		† 6 - 7†		Old Foresters
02.11.2013	Old Etonians		0 - 2		Old Tonbridgians
26.10.2013	Lancing Old Boys		2 - 1		Old Chigwellians
26.10.2013	Old Berkhamstedians		† 6 - 4†		Old Aldenhamians
26.10.2013	Old Brentwoods		H - W		Old Radleians
26.10.2013	Old Eastbournians		2 - 3		Old Bradfieldians
26.10.2013	Old King's Scholars		0 - 5		Old Carthusians
14.12.2013	Old Marlburians		0 - 4		Old Foresters
2nd Round
07.12.2013	Old Tonbridgians		4 - 0		Old Malvernians
14.12.2013	Old Salopians		6 - 1		Old Cholmeleians
11.01.2014	Old Westminsters		4 - 1		Old Haileyburians
14.12.2013	Old Carthusians		5 - 0		Old Wykehamists
14.12.2013	Lancing Old Boys		W - L		Old Bradfieldians
14.12.2013	Old Berkhamstedians		2 - 8		Old Reptonians
22.02.2014	Old Brentwoods		† 4 - 4†		Old Foresters
14.12.2013	Old Epsomians		L - W		Old Brentwoods
3rd Round
15.02.2014	Old Tonbridgians		3 - 0		Old Salopians
15.02.2014	Old Westminsters		0 - 5		Old Carthusians
01.03.2014	Lancing Old Boys		4 - 2		Old Reptonians
08.03.2014	Old Foresters		1 - 0		Old Brentwoods
Semi-Final
08.03.2014	Old Tonbridgians		1 - 2		Old Carthusians
26.03.2014	Lancing Old Boys		0 - 2		Old Foresters
Final (Merchant Taylors School, Northwood)
12.04.2014	Old Carthusians		†3 - 0†		Old Foresters