1st Round
02.11.2019	KCS Old Boys		10 - 0		Old Aldenhamians
19.10.2019	Old Alleynians		4 - 1		Old Merchant Taylors
19.10.2019	Old Amplefordians		†4 - 5†		Old Radleians
19.10.2019	Old Berkhamstedians		0 - 2		Old Tonbridgians
26.10.2019	Old Bradfieldians		4 - 0		Old Shirburnians
26.10.2019	Old Carthusians		9 - 0		Old Kingstonians
26.10.2019	Old Columbans		1 - 0		Old Brentwoods
12.10.2019	Old Etonians		0 - 3		Old Harrovians
19.10.2019	Old Foresters		2 - 1		Old Marlburians
09.11.2019	Old Malvernians		1 - 3		Old Kimboltonians
19.10.2019	Old Reptonians		8 - 0		Old Eastbournians
26.10.2019	Old Rugbeians		†5 - 1†		Old Bancroftians
26.10.2019	Old Salopians		7 - 1		Lancing Old Boys
09.11.2019	Old Sennockians		0 - 1		Old Wykehamists
12.10.2019	Old Westminsters		4 - 2		Old Chigwellians
2nd Round
21.12.2019	Old Alleynians		1 - 0		Old Salopians
21.12.2019	Old Carthusians		7 - 0		Old Radleians
14.12.2019	Old Foresters		0 - 5		Old Bradfieldians
14.12.2019	Old Harrovians		†2 - 3†		KCS Old Boys
04.01.2020	Old Kimboltonians		2 - 1		Old Columbans
21.12.2019	Old Suttonians		1 - 5		Old Reptonians
14.12.2019	Old Westminsters		†2 - 3†		Old Rugbeians
21.12.2019	Old Wykehamists		1 - 6		Old Tonbridgians
Quarter-Finals
22.02.2020	Old Bradfieldians		5 - 1		Old Rugbeians
15.02.2020	Old Kimboltonians		1 - 2		Old Tonbridgians
08.02.2020	Old Reptonians		3 - 1		KCS Old Boys
15.02.2020	Old Alleynians		2 - 3		Old Carthusians
Semi-Final
05.09.2020	Old Bradfieldians		†1 - 1†		Old Tonbridgians
19.09.2020	Old Tonbridgians		0 - 1		Old Bradfieldians
14.03.2020	Old Reptonians		†0 - 0†		Old Carthusians
26.09.2020	Old Carthusians		3 - 0		Old Reptonians
Final (Merchant Taylors School, Northwood)
24.10.2020	Old Bradfieldians		0 - 2		Old Carthusians