About this time, while the Araucanians were valiantly endeavouring to oppose the Spanish arms, the English also planned an expedition against them in that remote quarter of the world. Sir Thomas Cavendish sailed with this view from Plymouth on the 21st of July 1586 with three ships, and arrived on the coast of Chili in the following year. He landed at the desert port of Quintero90, and endeavoured to enter into a negociation with the natives of the country; but he was attacked by Alonzo Molina, the corregidor of St Jago, and compelled to reimbark with the loss of several soldiers and seamen, and quitted the coast after a very short stay.

Cadeguala, the new toqui, signalized the commencement of his administration by several successful inroads into the Spanish possessions, the particulars of which are not recorded. Having notice of the alarm in Spanish Chili occasioned by the English squadron, he resolved to avail himself of that diversion of the Spanish forces to make an effort against the city of Angol by surprise. He maintained a secret intelligence with some of the inhabitants of that place, by whose means he prevailed upon a number of native Chilese, who were in the service of the Spanish citizens, to set fire to their masters houses at a certain hour of an appointed night, when he was to be ready with his army at the gates to assault the place. His plan was accordingly executed; and entering the city during the confusion occasioned by the fires, he divided his force, consisting of a thousand foot and an hundred horse, into several detachments, which made a horrible carnage of the citizens, who flying from the flames fell into the hands of the Araucanians. The garrison attempted in vain to dislodge the enemy, and the whole population of the place had been assuredly put to the sword, but for the courage and conduct of the governor, who had fortunately arrived at the city only two hours before the attack. He immediately hastened with his guards to the different quarters which were occupied by the enemy, where with wonderful presence of mind he collected the dispersed inhabitants who had escaped the sword of the enemy, and conducted them to the citadel. Having armed and marshalled all the most resolute of the inhabitants, he sallied out from the citadel at their head against the enemy, whom he compelled to evacuate the city at break of day. It would appear that the Araucanians had now become less scrupulous than formerly in their mode of making war; for Cadeguala was not abandoned by any of his officers on this occasion, as Caupolican had formerly been in his attempt to surprise Canete by similar means.

Although the Arancanian general had not succeeded in this daring enterprise according to his expectations, he was so little discouraged by its failure that he immediately undertook the siege of Puren, which appeared more easy to be taken as it was situated at some distance from the Spanish frontiers. He accordingly invested it regularly with four thousand men in four separate divisions, under the respective commands of Guanoalca, Caniotaru, Relmuantu, and Curilemu, the most valiant officers of his army. On receiving notice of the investiture of Puren, the governor hastened to its relief with a strong reinforcement, but was opposed on his march by Cadeguala at the head of an hundred and fifty Araucanian horse armed with lances, and compelled to retreat after a long and obstinate combat, in which several fell on both sides. Elated by this success, the toqui made proposals to the besieged, either to enter into his service or to allow them to retire unmolested. These terms, which he pretended were very advantageous for men in their situation, were disdainfully rejected; yet one man of the garrison, named Juan Tapia, went over to the Araucanians by whom he was well received, and even got advancement in their army. As these terms were rejected, Cadeguala determined to endeavour to shorten the siege in a different manner. He presented himself one day before the walls mounted on a fine horse which he had taken from the governor, and boldly defied Garcia Ramon the commander of the garrison to single combat at the end of three days. The challenge was accepted, and the intrepid toqui appeared in the field at the time appointed, with a small number of attendants, whom he placed apart. Ramon likewise came out from the fort to meet him, attended by an escort of forty men, whom he ordered to remain at some distance. The two champions, having taken their distance set spurs to their horses and ran their course with such fury that Cadeguala fell at the first rencounter, pierced through the body by the lance of his adversary. He refused however to acknowledge himself vanquished, and even endeavoured to remount his horse to renew the combat, but died in the attempt. His attendants hastened to raise him, and even carried off his body after a sharp contest with the Spaniards.

After the death of their commander, the Araucanians retired from the blockade for a short time; but soon returned to the siege, after having elected Guanoalca to the vacant toquiate, having been informed by the Spanish deserter Tapia, that the garrison was ill supplied with provisions, and divided into parties. Cut off from all hopes of relief, and dissatisfied with the conduct of their officers, the besieged soon determined upon evacuating the place; and the Araucanians allowed them to march off unmolested, according to their usual policy. Guanoalca immediately marched against another fort which the Spaniards had recently erected in the neighbourhood of Mount Mariguenu; but finding that it had been recently and considerably reinforced, he proceeded against the forts of Trinidad and Spiritu Santo on the banks of the Biobio. As the governor of Chili was apprehensive that he might not be able to defend these forts, or perhaps considered them of too little importance to hazard the safety of their garrisons, he evacuated them in 1589, and transferred their garrisons to another fortress which he directed to be constructed on the river Puchanqui as a protection for the city of Angol, so that the operations of the war consisted mostly in the construction and demolition of fortifications.

The toquiate of Guanoalca was more remarkable for the exploits of a heroine named Janequeo than by his own. This famous woman was wife of Guepotan, a valiant officer who had long defended the fortified post of Liben near Villarica. After the loss of that important place he retired to the Andes, where he used every effort to stimulate the Puelches inhabiting that mountainous region to rise in defence of the country against the Spanish invaders. Being desirous of having his wife along with him, he descended into the plains in search of her, but was surprised by a party of Spaniards, and preferring to be cut in pieces rather than yield himself a prisoner, he was slain in the unequal combat. Janequeo, inflamed by an ardent desire to revenge the death of her husband, put herself at the head of an army of Puelches in 1590, assisted by Guechiuntereo her brother, with which she made inroads into the Spanish settlements, killing all of that nation who fell into her hands. Reinforced by a regiment of veteran soldiers which had been sent him from Peru, the governor Don Alonza Sotomayor, marched against the heroine; but, by constantly occupying the high grounds, attacking sometimes the van, sometimes the rear of the Spaniards, and harassing them in every possible way, she at last obliged the governor to retire, after having lost much time and a considerable number of men to no purpose. As the governor was of opinion that rigorous measures were best calculated to quell the pride of the Araucanians, he ordered all the prisoners taken in this incursion to be hung before his retreat. On this occasion, one of these men requested to be hanged on a higher tree than the rest, that the sacrifice he had made of himself for his country might be the more conspicuous, and inspire his surviving countrymen with the more ardent determination to defend their liberties.