1st Round
24.10.2020	Old Merchant Taylors		0 - 7		Old Etonians
17.10.2020	Old Salopians		4 - 0		Old Shirburnians
31.10.2020	Old Kimboltonians		1 - 1		Old Aldenhamians
05.12.2020	Old Aldenhamians		1 - 2		Old Kimboltonians
31.10.2020	Old Malvernians		2 - 0		Old Harrovians
24.10.2020	Old Westminsters		†3 - 6†		Old Suttonians
31.10.2020	Old Amplefordians		1 - 7		KCS Old Boys
31.10.2020	Old Sennockians		5 - 3		Old Berkhamstedians
24.10.2020	Old Chigwellians		†3 - 4†		Old Tonbridgians
24.10.2020	Old Alleynians		4 - 1		Old Columbans
17.10.2020	Old Carthusians		4 - 0		Old Rugbeians
17.10.2020	Old Radleians		1 - 2		Old Cholmeleians
24.10.2020	Old Wykehamists		†2 - 1†		Old Brentwoods
17.10.2020	Old Reptonians		W - L		Old Marlburians
17.10.2020	Old Eastbournians		0 - 10		Old Bradfieldians
24.10.2020	Old Foresters		10 - 0		Old Bancroftians
24.10.2020	Old Kingstonians		1 - 2		Lancing Old Boys
2nd Round
19.12.2020	Old Alleynians		W - L		Old Carthusians
24.04.2021	Old Cholmeleians		(3)†2 - (4)2†		Old Wykehamists
17.04.2021	Old Etonians		0 - 1		Old Salopians
17.04.2021	Old Foresters		5 - 1		Lancing Old Boys
17.04.2021	Old Kimboltonians		5 - 3		Old Malvernians
19.12.2020	Old Reptonians		3 - 1		Old Bradfieldians
17.04.2021	Old Sennockians		0 - 6		Old Tonbridgians
19.12.2020	Old Suttonians		L - W		KCS Old Boys
Quarter-Finals
15.05.2021	KCS Old Boys		3 - 2		Old Tonbridgians
08.05.2021	Old Alleynians		5 - 3		Old Wykehamists
15.05.2021	Old Reptonians		†1 - 2†		Old Foresters
08.05.2021	Old Salopians		3 - 2		Old Kimboltonians
Semi-Final
22.05.2021	Old Alleynians		0 - 3		Old Foresters
22.05.2021	Old Salopians		3 - 2		KCS Old Boys
Final (Merchant Taylors School, Northwood)
29.05.2021	Old Salopians		2 - 4		Old Foresters