The competition was suspended from 1939-1946 due to World War II

Senior Cup 1946-1947
Round 1
	Old Mercers		Brighton Old Grammarians	W―L
	Old Libertians		Old Grammarians	2―3
	Old Oxford Citizens		Old Derbeians	L―W
	Old Owens		Alleyn Old Boys	5―3
	Old Bromleians		Old Westminster Citizens	3―3, 1―4
	Old Stationers		Old Colfeians	12―0
	Old Olavians		Old Finchleians	L―W
	Old Guildfordians		Old Latymerians	0―8
Round 2
	Old Owens		Old Finchleians	8―1
	Old Grammarians		Old Latymerians	0―6
	Old Mercers		Old Stationers	1―5
	Old Derbeians		Old Westminster Citizens	1―2
Semi-Finals
	Old Westminster Citizens		Old Stationers	2―3
	Old Latymerians		Old Owens	4―2
Final
	Old Latymerians		Old Stationers	6―6 (shared)
Senior Cup 1947-1948
Round 1
	Old Stationers		Old Grammarians	5―3
	Alleyn Old Boys		Old Lyonians	2―0
	Old Colfeians		Old Wilsonians	0―3
	Old Mercers		Old Latymerians	1―1, 0―3
	Old Thorntonians		Old Bromleians	7―4
	Old Libertians		Old Finchleians	4―2
	Old Westminster Citizens		Old Guildfordians	W―L
	Old Owens		Old Derbeians	2―6
Round 2
	Old Wilsonians		Old Latymerians	1―7
	Old Libertians		Old Stationers	5―2
	Old Thorntonians		Old Derbeians	5―0
	Alleyn Old Boys		Old Westminster Citizens	3―1
Semi-Finals
	Old Libertians		Old Thorntonians	8―2
	Old Latymerians		Alleyn Old Boys	2―0
Final
	Old Libertians		Old Latymerians	5―2
Senior Cup 1948-1949
Round 1
	Old Mercers		Old Colfeians	2―5
	Old Owens		Old Parkonians	2―3
	Old Lyonians		Old Grammarians	4―3
	Alleyn Old Boys		Old Wilsonians	4―2
	Old Finchleians		Old Westminster Citizens	1―0
	Old Latymerians		Old Thorntonians	2―4
	Old Stationers		Old Derbeians	6―0
	Old Libertians		Old Bromleians	1―1, 3―2
Round 2
	Old Stationers		Old Finchleians	3―2
	Alleyn Old Boys		Old Parkonians	0―1
	Old Lyonians		Old Colfeians	0―1
	Old Libertians		Old Thorntonians	0―1
Semi-Finals
	Old Stationers		Old Parkonians	4―2
	Old Thorntonians		Old Colfeians	4―1
Final
	Old Stationers		Old Thorntonians	3―1
Senior Cup 1949-1950
Round 1
	Old Thorntonians		Old Stationers	1―2
	Old Mercers		Old Westminster Citizens	0―2
	Old Bromleians		Old Libertians	2―2, 2―3
	Old Finchleians		Old Grammarians	3―2
	Old Latymerians		Old Parkonians	3―1
	Old Owens		Old Derbeians	3―1
	Old Wilsonians		Old Lyonians	6―2
	Old Colfeians		Alleyn Old Boys	0―1
Round 2
	Old Wilsonians		Alleyn Old Boys	1―2
	Old Westminster Citizens		Old Libertians	4―2
	Old Owens		Old Latymerians	1―1, 3―4
	Old Stationers		Old Finchleians	2―1
Semi-Finals
	Alleyn Old Boys		Old Westminster Citizens	4―2
	Old Latymerians		Old Stationers	5―2
Final
	Alleyn Old Boys		Old Latymerians	6―3