Following the start of the Apocalypse and in particular Sam saying "Yes" to Lucifer, Bobby worked with Dean and Castiel to protect what was left of humanity from the demons and the Croatoan zombies. To this end, he apparently helped to set up Camp Chitaqua and took a picture with Castiel and a few other hunters outside of it.
Bobby presumably was killed at some point before 2014. He was apparently shot to death in his house for an unknown reason and his wheelchair and possibly his body were left lying there, never recovered by Dean or his other friends.
When Dean arrived in 2014 from 2009 thanks to Zachariah, he traveled to Bobby's house and found it dusty and in a disarray with Bobby's wheelchair lying on its side with three bloody bullet holes in it. From Bobby's journal, Dean learned about Camp Chitaqua and its location and continued on to there.
- He is the first alternate counterpart of Bobby Singer introduced. The second is the Apocalypse World Bobby Singer, the third that was mentioned only is Alternate Bobby Singer and fourth being Future Bobby.
- He has the same history as Bobby Singer up until 2009.
- Unlike his Main Universe counterpart, his legs were never healed and he remained paralyzed given the existance of his wheelchair in his house and him sitting in it in the Camp Chitaqua picture.
- When Dean arrives at Bobby's house, its actually not clear if he finds Bobby's body or just his wheelchair. When Dean looks at the ground he goes "oh no" and turns the wheelchair over to show the three bullet holes. However, the ground in front of the wheelchair is not shown so its not actually clear if Bobby's dead body is lying there or not.