Senior Cup 1950-1951
Round 1
	Old Bromleians		Old Lyonians	4―1
	Alleyn Old Boys		Old Westminster Citizens	3―5
	Old Wilsonians		Old Stationers	1―4
	Old Latymerians		Old Libertians	0―3
	Old Thorntonians		Old Grammarians	3―0
	Old Derbeians		Old Mercers	8―0
	Old Owens		Old Parkonians	1―3
	Old Colfeians		Old Finchleians	1―2
Round 2
	Old Derbeians		Old Finchleians	1―2
	Old Bromleians		Old Parkonians	0―1
	Old Westminster Citizens		Old Thorntonians	6―2
	Old Libertians		Old Stationers	4―1
Semi-Finals
	Old Libertians		Old Westminster Citizens	4―3
	Old Parkonians		Old Finchleians	3―0
Final
	Old Parkonians		Old Libertians	3―1
Senior Cup 1951-1952
Preliminary Round
	Old Lyonians		Old Mercers	10―1
Round 1
	Old Latymerians		Alleyn Old Boys	3―2
	Old Colfeians		Old Finchleians	0―6
	Old Bromleians		Old Wilsonians	1―2
	Old Owens		Old Lyonians	2―3
	Old Libertians		Old Derbeians	4―0
	Old Westminster Citizens		Old Parkonians	1―2
	Old Thorntonians		Old Grocers	2―0
	Old Grammarians		Old Stationers	6―5
Round 2
	Old Wilsonians		Old Thorntonians	2―0
	Old Grammarians		Old Latymerians	2―4
	Old Parkonians		Old Finchleians	4―1
	Old Lyonians		Old Libertians	2―4
Semi-Finals
	Old Libertians		Old Latymerians	5―0
	Old Parkonians		Old Wilsonians	2―1
Final
	Old Parkonians		Old Libertians	5―1
Junior Cup 1951-1952
Round 1
	Old Stationers 2nd		Old Westminster Citizens 2nd	1―3
	Old Bromleians 2nd		Old Colfeians 2nd	3―1
	Old Parkonians 2nd		Old Latymerians 2nd	5―4
	Old Wilsonians 2nd		Alleyn Old Boys 2nd	4―1
	Old Finchleians 2nd		Old Lyonians 2nd	5―1
	Old Grammarians 2nd		Old Mercers 2nd	5―1
	Old Libertians 2nd		Old Thorntonians 2nd	3―1
Round 2
	Old Grocers 2nd		Old Grammarians 2nd	3―5
	Old Wilsonians 2nd		Old Parkonians 2nd	8―3
	Old Bromleians 2nd		Old Libertians 2nd	0―3
	Old Finchleians 2nd		Old Westminster Citizens 2nd	5―4
Semi-Finals
	Old Grammarians 2nd		Old Libertians 2nd	4―0
	Old Wilsonians 2nd		Old Finchleians 2nd	0―3
Final
	Old Finchleians 2nd		Old Grammarians 2nd	4―3
Senior Cup 1952-1953
Preliminary Round
	Old Grocers		Old Latymerians	0―2
	Alleyn Old Boys		Old Owens	3―2
Round 1
	Old Parkonians		Old Minchendenians	4―0
	Old Westminster Citizens		Old Latymerians	3―2
	Old Thorntonians		Old Bromleians	0―4
	Old Derbeians		Old Libertians	1―2
	Old Mercers		Old Lyonians	1―3
	Old Wilsonians		Old Colfeians	5―1
	Old Finchleians		Old Grammarians	2―0
	Alleyn Old Boys		Old Stationers	3―2
Round 2
	Old Westminster Citizens		Alleyn Old Boys	0―3
	Old Finchleians		Old Lyonians	2―7
	Old Parkonians		Old Wilsonians	6―4
	Old Bromleians		Old Libertians	4―4, 1―4
Semi-Finals
	Alleyn Old Boys		Old Parkonians	3―2
	Old Libertians		Old Lyonians	3―0
Final
	Old Libertians		Alleyn Old Boys	4―0
Junior Cup 1952-1953
Preliminary Round
	Alleyn Old Boys 2nd		Old Minchendenians 2nd	0―7
Round 1
	Old Latymerians 2nd		Old Minchendenians 2nd	2―4
	Old Lyonians 2nd		Old Mercers 2nd	5―2
	Old Libertians 2nd		Old Thorntonians 2nd	1―2
	Old Westminster Citizens 2nd		Old Grammarians 2nd	2―0
	Old Wilsonians 2nd		Old Bromleians 2nd	1―6
	Old Owens 2nd		Old Grocers 2nd	0―4
	Old Parkonians 2nd		Old Stationers 2nd	2―0
	Old Colfeians 2nd		Old Finchleians 2nd	2―3
Round 2
	Old Grocers 2nd		Old Lyonians 2nd	6―1
	Old Westminster Citizens 2nd		Old Minchendenians 2nd	5―1
	Old Parkonians 2nd		Old Bromleians 2nd	0―1
	Old Finchleians 2nd		Old Thorntonians 2nd	3―2
Semi-Finals
	Old Finchleians 2nd		Old Grocers 2nd	5―1
	Old Bromleians 2nd		Old Westminster Citizens 2nd	6―7
Final
	Old Westminster Citizens 2nd		Old Finchleians 2nd	2―1
Senior Cup 1953-1954
Preliminary Round
	Old Stationers		Alleyn Old Boys	3―1
	Old Grocers		Old Grammarians	1―3
Round 1
	Old Grammarians		Old Libertians	2―3
	Old Stationers		Old Finchleians	3―2
	Old Latymerians		Old Colfeians	3―3, 0―3
	Old Wilsonians		Old Derbeians	6―4
	Old Minchendenians		Old Mercers	8―1
	Old Westminster Citizens		Old Parkonians	4―1
	Old Owens		Old Thorntonians	1―8
	Old Bromleians		Old Lyonians	9―0
Round 2
	Old Thorntonians		Old Wilsonians	5―2
	Old Minchendenians		Old Stationers	4―5
	Old Libertians		Old Westminster Citizens	1―1, 2―3
	Old Bromleians		Old Colfeians	2―0
Semi-Finals
	Old Bromleians		Old Thorntonians	5―1
	Old Westminster Citizens		Old Stationers	1―3
Final
	Old Bromleians		Old Stationers	3―2
Junior Cup 1953-1954
Round 1
	Old Grocers 2nd		Old Lyonians 2nd	3―2
	Old Stationers 2nd		Old Libertians 2nd	W―L
	Alleyn Old Boys 2nd		Old Thorntonians 2nd	4―3
	Old Grammarians 2nd		Old Mercers 2nd	4―1
	Old Latymerians 2nd		Old Westminster Citizens 2nd	6―1
	Old Colfeians 2nd		Old Bromleians 2nd	3―4
	Old Parkonians 2nd		Old Owens 2nd	2―0
	Old Finchleians 2nd		Old Minchendenians 2nd	7―3
Round 2
	Old Stationers 2nd		Old Parkonians 2nd	5―1
	Old Latymerians 2nd		Old Grocers 2nd	4―0
	Old Bromleians 2nd		Old Finchleians 2nd	2―5
	Alleyn Old Boys 2nd		Old Grammarians 2nd	5―4
Semi-Finals
	Alleyn Old Boys 2nd		Old Finchleians 2nd	2―1
	Old Stationers 2nd		Old Latymerians 2nd	3―0
Final
	Old Stationers 2nd		Alleyn Old Boys 2nd	2―2, 0―1
Minor Cup 1953-1954
Round 1
	Old Libertians 3rd		Old Grammarians 3rd	0―1
	Old Latymerians 3rd		Old Finchleians 3rd	3―2
	Old Owens 3rd		Old Wilsonians 3rd	2―4
	Old Thorntonians 3rd		Alleyn Old Boys 3rd	2―7
	Old Stationers 3rd		Old Parkonians 3rd	1―2
	Old Westminster Citizens 3rd		Old Lyonians 3rd	9―1
	Old Bromleians 3rd		Old Colfeians 3rd	9―2
	Old Minchendenians 3rd		Old Mercers 3rd	4―2
Round 2
	Old Grammarians 3rd		Alleyn Old Boys 3rd	0―0, L―W
	Old Parkonians 3rd		Old Westminster Citizens 3rd	5―4
	Old Latymerians 3rd		Old Minchendenians 3rd	4―0
	Old Wilsonians 3rd		Old Bromleians 3rd	1―2
Semi-Finals
	Old Latymerians 3rd		Old Bromleians 3rd	6―1
	Alleyn Old Boys 3rd		Old Parkonians 3rd	5―3
Final
	Old Latymerians 3rd		Alleyn Old Boys 3rd	2―0
Senior Cup 1954-1955
Preliminary Round
	Old Thorntonians		Old Mercers	6―3
Round 1
	Old Libertians		Old Wilsonians	2―4
	Old Westminster Citizens		Old Grammarians	4―1
	Old Parkonians		Old Derbeians	4―1
	Old Colfeians		Old Stationers	1―4
	Old Finchleians		Old Latymerians	4―2
	Alleyn Old Boys		Old Bromleians	2―1
	Old Thorntonians		Old Owens	1―4
	Old Minchendenians		Old Lyonians	6―2
Round 2
	Old Parkonians		Alleyn Old Boys	2―3
	Old Stationers		Old Westminster Citizens	1―0
	Old Minchendenians		Old Finchleians	4―3
	Old Wilsonians		Old Owens	0―3
Semi-Finals
	Alleyn Old Boys		Old Stationers	5―3
	Old Owens		Old Minchendenians	0―4
Final
	Alleyn Old Boys		Old Minchendenians	3―2
Junior Cup 1954-1955
Round 1
	Old Finchleians 2nd		Old Lyonians 2nd	6―1
	Old Parkonians 2nd		Old Stationers 2nd	3―0
	Old Mercers 2nd		Old Colfeians 2nd	1―3
	Alleyn Old Boys 2nd		Old Grammarians 2nd	8―3
	Old Westminster Citizens 2nd		Old Minchendenians 2nd	1―3
	Old Owens 2nd		Old Thorntonians 2nd	6―1
	Old Bromleians 2nd		Old Latymerians 2nd	3―4
Round 2
	Old Latymerians 2nd		Old Finchleians 2nd	4―1
	Old Parkonians 2nd		Old Libertians 2nd	9―9, 1―0
	Old Colfeians 2nd		Alleyn Old Boys 2nd	1―4
	Old Minchendenians 2nd		Old Owens 2nd	6―1
Semi-Finals
	Alleyn Old Boys 2nd		Old Parkonians 2nd	8―0
	Old Minchendenians 2nd		Old Latymerians 2nd	4―6
Final
	Alleyn Old Boys 2nd		Old Latymerians 2nd	2―1
Minor Cup 1954-1955
Round 1
	Old Wilsonians 3rd		Old Parkonians 3rd	0―7
	Old Bromleians 3rd		Old Finchleians 3rd	5―1
	Old Latymerians 3rd		Old Owens 3rd	4―0
	Old Colfeians 3rd		Old Minchendenians 3rd	0―1
	Old Lyonians 3rd		Old Mercers 3rd	2―1
	Old Grammarians 3rd		Alleyn Old Boys 3rd	2―0
	Old Libertians 3rd		Old Westminster Citizens 3rd	1―5
	Old Stationers 3rd		Old Thorntonians 3rd	11―0
Round 2
	Old Stationers 3rd		Old Minchendenians 3rd	3―4
	Old Grammarians 3rd		Old Latymerians 3rd	4―1
	Old Westminster Citizens 3rd		Old Bromleians 3rd	4―1
	Old Lyonians 3rd		Old Parkonians 3rd	0―3
Semi-Finals
	Old Westminster Citizens 3rd		Old Parkonians 3rd	1―0
	Old Grammarians 3rd		Old Minchendenians 3rd	3―6
Final
	Old Westminster Citizens 3rd		Old Minchendenians 3rd	3―0
Senior Cup 1955-1956
Preliminary Round
	Old Mercers		Old Stationers	2―12
Round 1
	Old Bromleians		Old Lyonians	0―3
	Old Thorntonians		Old Libertians	3―5
	Old Owens		Old Westminster Citizens	0―0, 2―8
	Old Wilsonians		Old Grammarians	5―3
	Old Minchendenians		Old Derbeians	7―0
	Old Colfeians		Old Parkonians	2―4
	Alleyn Old Boys		Old Stationers	3―2
	Old Finchleians		Old Latymerians	4―0
Round 2
	Old Lyonians		Alleyn Old Boys	0―3
	Old Westminster Citizens		Old Finchleians	5―2
	Old Libertians		Old Parkonians	2―2, 1―4
	Old Wilsonians		Old Minchendenians	1―5
Semi-Finals
	Alleyn Old Boys		Old Minchendenians	5―2
	Old Parkonians		Old Westminster Citizens	5―2
Final
	Old Parkonians		Alleyn Old Boys	1―0
Junior Cup 1955-1956
Round 1
	Old Lyonians 2nd		Old Bromleians 2nd	0―4
	Old Westminster Citizens 2nd		Old Latymerians 2nd	5―1
	Old Libertians 2nd		Old Stationers 2nd	0―1
	Old Owens 2nd		Old Mercers 2nd	0―1
	Old Colfeians 2nd		Old Grammarians 2nd	4―2
	Old Minchendenians 2nd		Old Parkonians 2nd	1―2
	Old Finchleians 2nd		Old Wilsonians 2nd	13―0
	Old Thorntonians 2nd		Alleyn Old Boys 2nd	1―5
Round 2
	Old Colfeians 2nd		Old Finchleians 2nd	0―5
	Old Parkonians 2nd		Old Mercers 2nd	3―1
	Old Westminster Citizens 2nd		Alleyn Old Boys 2nd	5―1
	Old Stationers 2nd		Old Bromleians 2nd	5―2
Semi-Finals
	Old Stationers 2nd		Old Westminster Citizens 2nd	3―8
	Old Parkonians 2nd		Old Finchleians 2nd	3―1
Final
	Old Westminster Citizens 2nd		Old Parkonians 2nd	2―1
Minor Cup 1955-1956
Round 1
	Old Finchleians 3rd		Old Minchendenians 3rd	4―2
	Old Owens 3rd		Old Stationers 3rd	2―9
	Old Colfeians 3rd		Old Westminster Citizens 3rd	2―7
	Old Grammarians 3rd		Old Latymerians 3rd	0―4
	Alleyn Old Boys 3rd		Old Mercers 3rd	2―0
	Old Parkonians 3rd		Old Thorntonians 3rd	8―0
	Old Libertians 3rd		Old Lyonians 3rd	3―4
Round 2
	Old Parkonians 3rd		Old Westminster Citizens 3rd	3―4
	Alleyn Old Boys 3rd		Old Latymerians 3rd	4―1
	Old Finchleians 3rd		Old Bromleians 3rd	2―4
	Old Stationers 3rd		Old Lyonians 3rd	3―1
Semi-Finals
	Alleyn Old Boys 3rd		Old Bromleians 3rd	3―3, 0―3
	Old Westminster Citizens 3rd		Old Stationers 3rd	6―4
Final
	Old Westminster Citizens 3rd		Old Bromleians 3rd	1―0
Senior Cup 1956-1957
Preliminary Round
	Alleyn Old Boys		Old Finchleians	0―2
Round 1
	Old Libertians		Old Bromleians	3―4
	Old Derbeians		Old Wilsonians	1―5
	Old Owens		Old Lyonians	4―2
	Old Latymerians		Old Finchleians	3―5
	Old Grammarians		Old Westminster Citizens	1―2
	Old Parkonians		Old Thorntonians	7―0
	Old Minchendenians		Old Colfeians	7―2
	Old Mercers		Old Stationers	0―6
Round 2
	Old Bromleians		Old Finchleians	2―4
	Old Owens		Old Stationers	0―8
	Old Westminster Citizens		Old Wilsonians	7―2
	Old Parkonians		Old Minchendenians	4―4, 4―1
	Old Minchendenians		Old Parkonians	1―4
Semi-Finals
	Old Stationers		Old Westminster Citizens	4―3
	Old Parkonians		Old Finchleians	0―2
Final
	Old Finchleians		Old Stationers	3―2
Junior Cup 1956-1957
Round 1
	Old Latymerians 2nd		Old Parkonians 2nd	3―0
	Old Stationers 2nd		Old Libertians 2nd	3―1
	Old Thorntonians 2nd		Old Mercers 2nd	3―4
	Old Finchleians 2nd		Old Wilsonians 2nd	5―3
	Old Lyonians 2nd		Old Owens 2nd	2―1
	Old Westminster Citizens 2nd		Alleyn Old Boys 2nd	3―2
	Old Bromleians 2nd		Old Minchendenians 2nd	5―1
	Old Colfeians 2nd		Old Grammarians 2nd	2―4
Round 2
	Old Bromleians 2nd		Old Mercers 2nd	2―1
	Old Latymerians 2nd		Old Stationers 2nd	3―2
	Old Finchleians 2nd		Old Grammarians 2nd	6―3
	Old Lyonians 2nd		Old Westminster Citizens 2nd	2―3
Semi-Finals
	Old Westminster Citizens 2nd		Old Bromleians 2nd	6―0
	Old Latymerians 2nd		Old Finchleians 2nd	7―1
Final
	Old Westminster Citizens 2nd		Old Latymerians 2nd	2―1
Minor Cup 1956-1957
Round 1
	Old Latymerians 3rd		Old Thorntonians 3rd	6―0
	Old Bromleians 3rd		Old Minchendenians 3rd	5―3
	Old Lyonians 3rd		Old Parkonians 3rd	2―7
	Old Stationers 3rd		Old Westminster Citizens 3rd	0―4
	Old Finchleians 3rd		Old Grammarians 3rd	W―L
	Old Mercers 3rd		Old Colfeians 3rd	5―10
	Alleyn Old Boys 3rd		Old Owens 3rd	5―1
Round 2
	Old Bromleians 3rd		Old Libertians 3rd	8―1
	Old Westminster Citizens 3rd		Alleyn Old Boys 3rd	3―1
	Old Colfeians 3rd		Old Finchleians 3rd	2―1
	Old Parkonians 3rd		Old Latymerians 3rd	2―3
Semi-Finals
	Old Bromleians 3rd		Old Westminster Citizens 3rd	1―4
	Old Latymerians 3rd		Old Colfeians 3rd	7―1
Final
	Old Latymerians 3rd		Old Westminster Citizens 3rd	5―1
Senior Cup 1957-1958
Preliminary Round
	Old Owens		Old Grammarians	1―3
Round 1
	Old Colfeians		Old Mercers	6―0
	Old Grammarians		Old Latymerians	5―1
	Old Westminster Citizens		Old Minchendenians	6―1
	Old Lyonians		Old Finchleians	1―2
	Old Wilsonians		Old Libertians	1―6
	Alleyn Old Boys		Old Derbeians	12―1
	Old Bromleians		Old Parkonians	2―4
	Old Thorntonians		Old Stationers	1―5
Round 2
	Old Stationers		Old Parkonians	3―2
	Alleyn Old Boys		Old Grammarians	4―1
	Old Westminster Citizens		Old Libertians	3―1
	Old Colfeians		Old Finchleians	0―2
Semi-Finals
	Old Finchleians		Old Westminster Citizens	3―0
	Alleyn Old Boys		Old Stationers	2―2, 0―10
Final
	Old Stationers		Old Finchleians	3―2
Junior Cup 1957-1958
Round 1
	Old Parkonians 2nd		Old Westminster Citizens 2nd	3―2
	Old Mercers 2nd		Old Bromleians 2nd	7―1
	Old Thorntonians 2nd		Old Latymerians 2nd	0―5
	Old Grammarians 2nd		Alleyn Old Boys 2nd	5―2
	Old Wilsonians 2nd		Old Lyonians 2nd	4―2
	Old Minchendenians 2nd		Old Libertians 2nd	3―5
	Old Finchleians 2nd		Old Owens 2nd	1―2
	Old Stationers 2nd		Old Colfeians 2nd	4―2
Round 2
	Old Grammarians 2nd		Old Libertians 2nd	8―1
	Old Parkonians 2nd		Old Owens 2nd	7―1
	Old Mercers 2nd		Old Latymerians 2nd	3―0
	Old Wilsonians 2nd		Old Stationers 2nd	3―4
Semi-Finals
	Old Mercers 2nd		Old Grammarians 2nd	0―2
	Old Parkonians 2nd		Old Stationers 2nd	4―1
Final
	Old Grammarians 2nd		Old Parkonians 2nd	5―2
Minor Cup 1957-1958
Round 1
	Old Minchendenians 3rd		Old Colfeians 3rd	3―2
	Old Owens 3rd		Alleyn Old Boys 3rd	0―2
	Old Westminster Citizens 3rd		Old Thorntonians 3rd	8―1
	Old Latymerians 3rd		Old Lyonians 3rd	1―0
	Old Stationers 3rd		Old Mercers 3rd	4―2
	Old Parkonians 3rd		Old Bromleians 3rd	2―3
	Old Grammarians 3rd		Old Libertians 3rd	3―1
Round 2
	Old Bromleians 3rd		Old Latymerians 3rd	2―3
	Old Finchleians 3rd		Alleyn Old Boys 3rd	3―2
	Old Minchendenians 3rd		Old Grammarians 3rd	3―2
	Old Westminster Citizens 3rd		Old Stationers 3rd	3―0
Semi-Finals
	Old Latymerians 3rd		Old Minchendenians 3rd	1―3
	Old Westminster Citizens 3rd		Old Finchleians 3rd	4―1
Final
	Old Westminster Citizens 3rd		Old Minchendenians 3rd	5―2
Senior Cup 1958-1959
Preliminary Round
	Old Westminster Citizens		Old Derbeians	10―0
Round 1
	Old Parkonians		Old Colfeians	2―1
	Old Grammarians		Old Wilsonians	6―2
	Old Westminster Citizens		Alleyn Old Boys	1―5
	Old Latymerians		Old Stationers	1―2
	Old Finchleians		Old Lyonians	1―2
	Old Minchendenians		Old Libertians	10―1
	Old Owens		Old Thorntonians	6―2
	Old Bromleians		Old Mercers	6―1
Round 2
	Old Minchendenians		Old Lyonians	7―3
	Old Parkonians		Old Grammarians	3―2
	Old Owens		Old Bromleians	5―1
	Alleyn Old Boys		Old Stationers	3―2
Semi-Finals
	Old Minchendenians		Alleyn Old Boys	3―1
	Old Owens		Old Parkonians	1―3
Final
	Old Parkonians		Old Minchendenians	3―0
Junior Cup 1958-1959
Round 1
	Old Grammarians 2nd		Old Libertians 2nd	2―5
	Old Colfeians 2nd		Old Stationers 2nd	1―2
	Old Owens 2nd		Old Westminster Citizens 2nd	2―4
	Old Lyonians 2nd		Old Minchendenians 2nd	2―7
	Old Wilsonians 2nd		Alleyn Old Boys 2nd	1―7
	Old Mercers 2nd		Old Thorntonians 2nd	2―4
	Old Bromleians 2nd		Old Finchleians 2nd	4―7
	Old Parkonians 2nd		Old Latymerians 2nd	2―1
Round 2
	Old Stationers 2nd		Old Parkonians 2nd	1―4
	Old Libertians 2nd		Old Westminster Citizens 2nd	2―4
	Alleyn Old Boys 2nd		Old Finchleians 2nd	7―1
	Old Thorntonians 2nd		Old Minchendenians 2nd	2―1
Semi-Finals
	Old Thorntonians 2nd		Old Parkonians 2nd	0―6
	Alleyn Old Boys 2nd		Old Westminster Citizens 2nd	1―7
Final
	Old Parkonians 2nd		Old Westminster Citizens 2nd	1―0
Minor Cup 1958-1959
Round 1
	Old Bromleians 3rd		Old Minchendenians 3rd	2―3
	Old Thorntonians 3rd		Old Lyonians 3rd	2―4
	Old Finchleians 3rd		Old Grammarians 3rd	0―4
	Old Colfeians 3rd		Old Owens 3rd	2―1
	Old Latymerians 3rd		Old Parkonians 3rd	1―0
	Old Mercers 3rd		Old Westminster Citizens 3rd	1―3
	Old Libertians 3rd		Alleyn Old Boys 3rd	3―1
Round 2
	Old Grammarians 3rd		Old Colfeians 3rd	2―3
	Old Latymerians 3rd		Old Stationers 3rd	1―2
	Old Libertians 3rd		Old Westminster Citizens 3rd	0―2
	Old Lyonians 3rd		Old Minchendenians 3rd	4―2
Semi-Finals
	Old Colfeians 3rd		Old Stationers 3rd	0―3
	Old Lyonians 3rd		Old Westminster Citizens 3rd	4―2
Final
	Old Stationers 3rd		Old Lyonians 3rd	2―1
Senior Cup 1959-1960
Round 1
	Old Libertians		Old Stationers	0―7
	Old Lyonians		Old Parkonians	4―6
	Alleyn Old Boys		Old Minchendenians	5―1
	Old Westminster Citizens		Old Mercers	7―0
	Old Thorntonians		Old Colfeians	1―3
	Old Latymerians		Old Grammarians	2―1
	Old Owens		Old Bromleians	0―10
	Old Finchleians		Old Wilsonians	6―2
Round 2
	Old Westminster Citizens		Old Finchleians	0―4
	Old Colfeians		Alleyn Old Boys	2―3
	Old Bromleians		Old Stationers	5―3
	Old Parkonians		Old Latymerians	2―0
Semi-Finals
	Old Parkonians		Old Finchleians	3―5
	Alleyn Old Boys		Old Bromleians	3―2
Final
	Alleyn Old Boys		Old Finchleians	3―2
Junior Cup 1959-1960
Round 1
	Old Colfeians 2nd		Old Minchendenians 2nd	2―1
	Alleyn Old Boys 2nd		Old Westminster Citizens 2nd	1―1, 1―6
	Old Stationers 2nd		Old Owens 2nd	4―1
	Old Latymerians 2nd		Old Grammarians 2nd	3―4
	Old Wilsonians 2nd		Old Libertians 2nd	1―2
	Old Mercers 2nd		Old Parkonians 2nd	1―5
	Old Bromleians 2nd		Old Lyonians 2nd	0―2
	Old Finchleians 2nd		Old Thorntonians 2nd	4―1
Round 2
	Old Stationers 2nd		Old Colfeians 2nd	1―0
	Old Libertians 2nd		Old Westminster Citizens 2nd	1―4
	Old Lyonians 2nd		Old Grammarians 2nd	3―7
	Old Parkonians 2nd		Old Finchleians 2nd	2―6
Semi-Finals
	Old Grammarians 2nd		Old Stationers 2nd	2―3
	Old Finchleians 2nd		Old Westminster Citizens 2nd	1―2
Final
	Old Westminster Citizens 2nd		Old Stationers 2nd	2―1
Minor Cup 1959-1960
Round 1
	Alleyn Old Boys 3rd		Old Grammarians 3rd	3―6
	Old Parkonians 3rd		Old Libertians 3rd	3―2
	Old Mercers 3rd		Old Latymerians 3rd	0―3
	Old Wilsonians 3rd		Old Lyonians 3rd	2―1
	Old Minchendenians 3rd		Old Westminster Citizens 3rd	1―2
	Old Bromleians 3rd		Old Owens 3rd	5―3
	Old Thorntonians 3rd		Old Finchleians 3rd	4―5
	Old Colfeians 3rd		Old Stationers 3rd	4―2
Round 2
	Old Finchleians 3rd		Old Wilsonians 3rd	4―0
	Old Colfeians 3rd		Old Grammarians 3rd	1―11
	Old Parkonians 3rd		Old Latymerians 3rd	8―3
	Old Bromleians 3rd		Old Westminster Citizens 3rd	3―1
Semi-Finals
	Old Bromleians 3rd		Old Parkonians 3rd	0―2
	Old Finchleians 3rd		Old Grammarians 3rd	2―4
Final
	Old Grammarians 3rd		Old Parkonians 3rd	3―1