written by John Punshon
Sources: The Sun, VASFA Year Book 1959

Home Team		v		Away Team
Section A
Friday, January 16, 1959. Showgrounds, Ascot Vale.
George Cross	0	-	0	JUST
Friday, January 23, 1959. Showgrounds, Ascot Vale.
Juventus	2	-	1	Moreland
Friday, January 30, 1959. Showgrounds, Ascot Vale.
Juventus Awarded to George Cross (Juventus had allowed a player to return to the field after he had been substituted while receiving treatment for an injury). Original score was Juventus 3 George Cross 2.	0	-	0	George Cross Awarded to George Cross (Juventus had allowed a player to return to the field after he had been substituted while receiving treatment for an injury). Original score was Juventus 3 George Cross 2.
Friday, February 6, 1959. Showgrounds, Ascot Vale.
Moreland	1	-	1	JUST
Friday, February 13, 1959. Showgrounds, Ascot Vale.
Juventus	1	-	2	JUST
Friday, February 20, 1959. Showgrounds, Ascot Vale.
Moreland	2	-	2	George Cross
Section B
Friday, January 16, 1959. Showgrounds, Ascot Vale.
Wilhelmina	3	-	1	Maribyrnong-Polonia
Friday, January 23, 1959. Showgrounds, Ascot Vale.
Hakoah	2	-	2	Slavia Port Melbourne
Friday, January 30, 1959. Showgrounds, Ascot Vale.
Wilhelmina	3	-	2	Hakoah
Friday, February 6, 1959. Showgrounds, Ascot Vale.
Slavia Port Melbourne	1	-	0	Maribyrnong-Polonia
Friday, February 13, 1959. Showgrounds, Ascot Vale.
Wilhelmina	2	-	0	Slavia Port Melbourne
Friday, February 20, 1959. Showgrounds, Ascot Vale.
Maribyrnong-Polonia	0	-	4	Hakoah
Semi-Finals
Friday, February 27, 1959. Showgrounds, Ascot Vale.
Hakoah	0	-	4	JUST
Friday, February 27, 1959. Showgrounds, Ascot Vale.
Wilhelmina	1	-	2	George Cross
1959 The Sun Cup Final
Friday, March 6, 1959. Showgrounds, Ascot Vale.
George Cross Goals: McVean, Other scorer not known	2	-	1	JUST Goal: Marinovic