I believe you can only connect one wireless headset to an Apple device at a time, due to Bluetooth not allowing it. But you might be able to connect multiple wired headsets to an iPad at the same time, as long as you have a dongle that allows for multiple devices.
- Answered by Chayce P from Sherwood Park
- 14 Mar 2019
- Flag as inappropriate Answer (How many wireless headphones can be connected to the iPad Pro 11)