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Senior Cup 1920-1921
Round 1
	Old Framlinghamians		Old Owens	L―W
	Alleyn Old Boys		Old Chigwellians	7―0
Semi-Finals
	Old Lawrentians		Old Owens	1―6
	Alleyn Old Boys		Old Brentwoods	2―2, 0―4
Final
	Old Owens		Old Brentwoods	1―1, 4―1
Senior Cup 1921-1922
Round 1
	Old Grammarians		Old Fullerians	2―0
	Old Bancroftians		Old Colfeians	4―1
Round 2
	Old Grammarians		Old Burians	W―L
	Old Chigwellians		Old Bancroftians	1―2
	Old Brentwoods		Old Framlinghamians	7―0
	Alleyn Old Boys		Old Owens	2―2, 4―2
Semi-Finals
	Old Grammarians		Old Bancroftians	2―4
	Old Brentwoods		Alleyn Old Boys	1―2
Final
	Old Bancroftians		Alleyn Old Boys	4―0
Senior Cup 1922-1923
Round 1
	Old Grammarians		Old Framlinghamians	8―2
	Old Brentwoods		Old Owens	2―1
	Old Haberdashers		Old Fullerians	1―0
	Alleyn Old Boys		Old Bancroftians	4―10
Semi-Finals
	Old Grammarians		Old Brentwoods	4―0
	Old Haberdashers		Old Bancroftians	1―1, 1―5
Final
	Old Bancroftians		Old Grammarians	2―0
Senior Cup 1923-1924
Round 1
	Old Brentwoods		Alleyn Old Boys	0―2
Round 2
	Old Bancroftians		Old Haberdashers	10―1
	Oxford High School Old Boys		Old Derbeians	1―8
	Alleyn Old Boys		Old Grammarians	1―3
	Old Owens		Old Finchleians	1―3
Semi-Finals
	Old Bancroftians		Old Finchleians	5―3
	Old Grammarians		Old Derbeians	1―1, 2―3
Final
	Old Bancroftians		Old Derbeians	6―0
Senior Cup 1924-1925
Round 1
	Old Mercers		Old Finchleians	3―4
Round 2
	Oxford High School Old Boys		Old Finchleians	1―6
	Old Brentwoods		Old Chigwellians	5―1
	Alleyn Old Boys		Old Bancroftians	1―0
Semi-Finals
	Old Brentwoods		Old Finchleians	1―2
	Old Derbeians		Alleyn Old Boys	W―L
Final
	Old Derbeians		Old Finchleians	1―0
Senior Cup 1925-1926
Round 1
	Old Mid-Whitgiftians		Old Stationers	0―1
	Clove (Old Grocers)		Old Westminster Citizens	2―2
	Old Westminster Citizens		Clove (Old Grocers)	0―4
	Old Monovians		Old Tollingtonians	1―3
Round 2
	Old Stationers		Old Owens	3―4
	Old Grammarians		Old Guildfordians	W―L
	Clove (Old Grocers)		Old Brentwoods	1―0
	Old Ardinians		City of Oxford School Old Boys	4―1
	Old Tollingtonians		Old Tenisonians	2―2, 2―1
	Old Chigwellians		Old Bancroftians	1―2
	Old Finchleians		Alleyn Old Boys	?―?, 3―4
	Old Mercers		Old Derbeians	3―4
Round 3
	Old Owens		Old Grammarians	5―3
	Clove (Old Grocers)		Old Ardinians	0―6
	Alleyn Old Boys		Old Derbeians	3―2
	Old Tollingtonians		Old Bancroftians	3―6
Semi-Finals
	Old Owens		Old Ardinians	3―3
	Old Ardinians		Old Owens	1―3
	Old Bancroftians		Alleyn Old Boys	3―3
	Alleyn Old Boys		Old Bancroftians	2―5
Final
	Old Bancroftians		Old Owens	4―3
Senior Cup 1926-1927
Round 1
	Old Colfeians		Old Grammarians	1―3
	Old Mercers		Old Rutlishians	2―3
	Old Tenisonians		Old Finchleians	3―0
Round 2
	Alleyn Old Boys		Old Westminster Citizens	6―2
	Old Ardinians		Old Derbeians	8―4
	Old Chigwellians		Old Askeans	2―5
	Old Grammarians		Old Bancroftians	3―3, 1―12
	Old Tenisonians		Old Grocers	3―3, 2―4
	Old Tollingtonians		Old Rutlishians	1―3
	Old Stationers		Old Guildfordians	4―0
	Old Owens		Old Monovians	7―1
Round 3
	Old Grocers		Old Ardinians	2―9
	Old Bancroftians		Old Stationers	5―2
	Old Rutlishians		Old Askeans	5―3
	Alleyn Old Boys		Old Owens	3―2
Semi-Finals
	Old Rutlishians		Alleyn Old Boys	6―2
	Old Bancroftians		Old Ardinians	6―1
Final
	Old Bancroftians		Old Rutlishians	5―0
Senior Cup 1927-1928
Round 1
	Alleyn Old Boys		Old Derbeians	5―6
	Old Oxford Citizens		Old Colfeians	4―3
	Old Ardinians		Old Mercers	4―1
	Old Westminster Citizens		Old Chigwellians	8―2
	Old Owens		Old Bancroftians	2―8
Round 2
	Old Guildfordians		Old Westminster Citizens	1―3
	Old Bancroftians		Old Ardinians	2―2, 0―3
	Old Grammarians		Old Oxford Citizens	2―3
	Old Derbeians		Old Finchleians	1―6
Semi-Finals
	Old Ardinians		Old Westminster Citizens	4―2
	Old Oxford Citizens		Old Finchleians	W―L
Final
	Old Oxford Citizens		Old Ardinians	2―1
Senior Cup 1928-1929
Round 1
	Old Colfeians		Old Derbeians	5―1
	Old Ardinians		Old Westminster Citizens	3―2
	Old Owens		Old Stationers	1―1, W―L
	Old Stationers		Old Owens	1―10
Round 2
	Old Colfeians		Old Bancroftians	1―6
	Alleyn Old Boys		Old Ardinians	1―0
Semi-Finals
	Alleyn Old Boys		Old Bancroftians	3―1
Final
	Alleyn Old Boys		Old Owens	8―2
Senior Cup 1929-1930
Round 1
	Old Colfeians		Old Guildfordians	2―1
	Alleyn Old Boys		Old Derbeians	1―0
	Old Oxford Citizens		Old Owens	1―4
	Old Westminster Citizens		Old Mercers	11―2
	Old Bancroftians		Old Grammarians	7―3
	Old Chigwellians		Old Rutlishians	6―1
	Old Finchleians		Old Grocers	3―0
Round 2
	Old Colfeians		Old Finchleians	2―3
	Old Owens		Alleyn Old Boys	4―3
	Old Stationers		Old Westminster Citizens	2―2, 4―2
	Old Chigwellians		Old Bancroftians	3―1
Semi-Finals
	Old Chigwellians		Old Stationers	0―4
	Old Finchleians		Old Owens	1―0
Final
	Old Stationers		Old Finchleians	2―1