Thank you for contacting syncfusion support.
We have checked your reported requirement based on the provided screenshot and it can be achievable using ItemTemplate support in ListBox. However, we have faced some issue while creating the sample based on your requirement. And we have planned to include the fix for this issue in our upcoming patch release. Which is expected to be available in August 20th 2019, we will update you with the sample once the fix for the issue is available until then we appreciate your patience. You can track the status of this defect using below link from our feedback portal,
Regards, Sangeetha M