Tokhtamysh’s cavalry attacks the right flank and the center of Timur's army at the Terek River, in the North Caucasus.

However, some Golden Horde emirs go over to Timur's side, which helps Timur defeat the left flank of Tokhtamysh's army and then the whole army itself.

The victorious army of Timur pursues that of Tokhtamysh's, annihilating cities while staying on the Volga.

Timur in the same year also plunders Ukek, ...

…Majar, …

...and Azaq, and ...

Timur completes the destruction of Sarai, then relentlessly pursues Tokhtamysh westward, ultimately to the region of present Ukraine, fighting Georgian resistance on his way south.

Tokhtamysh, now a permanent fugitive, attempts a reconciliation with Timur but meets with little success.

Timur, in the second phase of the conflict with Tokhtamysh, takes a different route against the enemy by invading his realm  via the Caucasus region.

Tokhtamysh, has recovered his position since the setback in 1391, and in the spring of 1395 raids the Timurid territory of Shirvan.

Timur counterattacks, reconquering the area and raiding the Golden Horde's territories.

Bayezid has built Anadoluhisarı fortress between 1393 and 1394 on the Anatolian (Asian) side of the Bosporus, as part of preparations for the blockade of Constantinople, which begins in 1395.

Timur, having added the Caucasus region and mountainous northern Persia to his holdings, rests his troops here for about eight months, then returns to Samarkand to prepare for his invasion of India.

Jelena Gruba had first became Queen of Bosnia as consort to King Stephen Dabiša, who had ascended in 1391, on the death of his relative, King Stephen Tvrtko I of Bosnia.

While Dabiša is a Roman Catholic, it is not certain which religion Jelena practiced.

Their only surviving child is a daughter named Stana, mentioned in a charter by which Stephen Dabiša gave her an area in Zachlumia to govern.

The charter, issued on April 26, 1395, also says that the area is to be inherited by Juraj Radivojević, husband of Stana's daughter Vladava and thus grandson-in-law of King Dabiša and Queen Jelena.

Vladava and her husband had already had at least two children by the time the charter was issued, making the King and Queen great-grandparents.

Assuming that each of the three women—Jelena, Stana, and Vladava—married at the age of fifteen and became mothers by the age of sixteen, the Queen must be more than fifty years old when she succeeds her husband.

When Stephen Dabiša dies in September 1395, Jelena ceases to be queen consort.

Her husband had designated King Sigismund of Hungary, the husband of his cousin, Queen Mary, as his successor.

Mary, however, has predeceased Dabiša, dying in May the same year.

The Bosnian nobility refuse to recognize Sigismund as king, as his right had rested in his status as Mary's husband.

Instead, the nobility installs Jelena as the successor to her husband.

Thus, during her reign Bosnian nobility will grow in power independently from the crown.

Among these are Sandalj Hranić, Hrvoje Vukčić and Pavle Radenović who all rule their own demesnes independently from the Queen.

The Queen's demesne is a small territory in central Bosnia, while she loses direct control over the territories of Usora in the valley of the river of Sava.

On the other hand, Jelena's reign will see successful trade with the Republic of Ragusa.

John of Gaunt’s Rule Over Aquitaine and the Gascon Discontent (1389–1395)

After leaving Portugal for Aquitaine, John of Gaunt, Duke of Lancaster, remained in the province until returning to England in November 1389. This effectively removed him from the political turmoil in England, where King Richard II clashed with the Lords Appellant, led by John’s younger brother, Thomas of Woodstock, Duke of Gloucester.

John of Gaunt's Investiture as Duke of Aquitaine (March 1390)

• Upon his return to England, John of Gaunt was formally invested with the Duchy of Aquitaine in March 1390 by King Richard II.
• This appointment fulfilled John’s long-standing ambition for an overseas dominion but provoked resentmentamong the Gascon nobility.

Tensions in Aquitaine: Absentee Rule and Gascon Discontent

• Despite his new title, John of Gaunt did not immediately return to Aquitaine, instead governing through seneschals as an absentee Duke.
• His administration disappointed the local nobility, who had expected strong leadership from the English Crown itself.
• The Gascons resented the notion that Aquitaine was a fief that could be granted to a subject—traditionally, it had always been held directly by the King of England or his heir.

Crisis and John of Gaunt’s Return to Gascony (1394–1395)

• By 1394, dissatisfaction had reached a critical point, with threats of secession from the Gascon nobles.
• In response, John of Gaunt was forced to spend nearly a year (1394–95) in Gascony, attempting to restore authority and secure loyalty.
• His efforts to stabilize the duchy were largely unsuccessful, as resentment toward his rule persisted, contributing to the ongoing decline of English influence in France.

Impact and Consequences

• John of Gaunt’s ineffective administration of Aquitaine weakened English authority in Gascony, further eroding Plantagenet control in France.
• The Gascon nobles’ dissatisfaction foreshadowed future tensions, as English rule in Aquitaine continued to decline throughout the 15th century.
• Gaunt’s absence from England in 1394–95 also meant he played little role in Richard II’s growing political instability, which would ultimately lead to Richard’s deposition in 1399.

John of Gaunt’s tenure as Duke of Aquitaine (1390–1399) was marked by absentee rule, local resentment, and administrative failure, hastening the deterioration of English power in southwestern France.