Ivan the Terrible had four legitimate wives, three of them poisoned presumably by his enemies or the royal families, who wanted to promote their daughters to his brides.

Anastasia Romanovna (in 1547–1560, death):
Tsarevna Anna Ivanovna (10 August 1548 – 20 July 1550)
Tsarevna Maria Ivanovna (17 March 1551 – young)
Tsarevich Dmitri Ivanovich (October 1552 – 26 June 1553)
Tsarevich Ivan Ivanovich (28 March 1554 – 19 November 1581)
Tsarevna Eudoxia Ivanovna (26 February 1556 – June 1558)
Tsar Feodor I of Russia (31 May 1557 – 6 January 1598)
Maria Temryukovna (in 1561–1569, death):
Tsarevich Vasili Ivanovich (21 March 1563 – 3 May 1563)
Marfa Sobakina (28 October – 13 November 1571, death)
Anna Koltovskaya (in 1572, sent to monastery).
This was the last of his church-authorized weddings.
She was later canonized as Saint Daria.

Anna Vasilchikova (in 1575/76, sent to monastery)
Vasilisa Melentyeva (?
-1580)
Maria Nagaya (since 1580), widow:
Tsarevich Dmitri Ivanovich (19 October 1582 – 15 May 1591)
The marriage of Ivan with Vasilisa Melentyeva was questioned, but researchers have found documents confirming her special relationship with the tsar.

In 1581, Ivan beat his pregnant daughter-in-law, Yelena Sheremeteva, for wearing immodest clothing, which may have caused a miscarriage.
His second son, also named Ivan, upon learning of that, engaged in a heated argument with his father, which resulted in Ivan striking his son in the head with his pointed staff and fatally wounding him.
That event is depicted in the famous painting by Ilya Repin, Ivan the Terrible and his son Ivan on Friday, 16 November 1581, better known as Ivan the Terrible killing his son.
Ivan the Terrible had four legitimate wives, three of them poisoned presumably by his enemies or the royal families, who wanted to promote their daughters to his brides.
Anastasia Romanovna (in 1547–1560, death):
Tsarevna Anna Ivanovna (10 August 1548 – 20 July 1550)
Tsarevna Maria Ivanovna (17 March 1551 – young)
Tsarevich Dmitri Ivanovich (October 1552 – 26 June 1553)
Tsarevich Ivan Ivanovich (28 March 1554 – 19 November 1581)
Tsarevna Eudoxia Ivanovna (26 February 1556 – June 1558)
Tsar Feodor I of Russia (31 May 1557 – 6 January 1598)
Maria Temryukovna (in 1561–1569, death):
Tsarevich Vasili Ivanovich (21 March 1563 – 3 May 1563)
Marfa Sobakina (28 October – 13 November 1571, death)
Anna Koltovskaya (in 1572, sent to monastery). This was the last of his church-authorized weddings. She was later canonized as Saint Daria.
Anna Vasilchikova (in 1575/76, sent to monastery)
Vasilisa Melentyeva (?-1580)
Maria Nagaya (since 1580), widow:
Tsarevich Dmitri Ivanovich (19 October 1582 – 15 May 1591)
The marriage of Ivan with Vasilisa Melentyeva was questioned, but researchers have found documents confirming her special relationship with the tsar.
In 1581, Ivan beat his pregnant daughter-in-law, Yelena Sheremeteva, for wearing immodest clothing, which may have caused a miscarriage. His second son, also named Ivan, upon learning of that, engaged in a heated argument with his father, which resulted in Ivan striking his son in the head with his pointed staff and fatally wounding him. That event is depicted in the famous painting by Ilya Repin, Ivan the Terrible and his son Ivan on Friday, 16 November 1581, better known as Ivan the Terrible killing his son.
Ivan the Terrible