Toyotomi Hideyoshi made his first playable appearance in Sengoku BASARA 2. Hideyoshi is a rival of Oda Nobunaga and fights alongside his vassal Takenaka Hanbei. Hideyoshi was born a normal, if big, man, and became friends with Maeda Keiji early in his life. They were good friends who spent their days pulling pranks or defending the locals from bandits. Hideyoshi at one point fell in love with a woman named Nene. Although young and seemingly happy, his lifestyle soon changed after a single encounter with Matsunaga Hisahide. Hideyoshi, overestimating his own strength and ability, tried to investigate Hisahide's might. Overtaken by the enemy's forces, he was captured and forced to suffer through humiliating displays of his weakness. After Keiji rescued him, Hideyoshi came to the realization that strength and power meant everything in the world. He began to harbor an incredible ambition: to create a powerful country where people could stand for themselves and prosper. However, because of the scars left by the humiliation he suffered from Hisahide, Hideyoshi's mind had become stigmatized and fixated on his absolute desire for power. Hideyoshi was now willing to grow into the ruthless warlord he needed to be to realize his ambitions; going so far as to murdering his love Nene. Needless to say, his relationship with Keiji had become strained.

One of the few things that separated Hideyoshi and Nobunaga was that, despite being a ruthless warlord, Hideyoshi still maintained a show of charisma and care for his army. This simple yet major clash in views causes the two to see one another as rivals. After Nobunaga's assassination by Akechi Mitsuhide, Hideyoshi took the opportunity to position himself as Japan's most powerful warlord. Before his dream of a power-driven Japan came to fruition, Hideyoshi's vassal, Tokugawa Ieyasu, revolted and took his life.