- From North Carolina.
- Formed by Steve Dilling in 2010 as a part-time band to perform during open dates when his full-time band IIIrd Tyme Out was not touring. Original band: Dilling (banjo), Darrell Webb (mandolin, lead vocals) who fronts his own band, Skip Cherryholmes (guitar) who performs with Lou Reid and Carolina and is also Dilling’s son-in-law, Jason Moore (bass) who is a member of Mountain Heart, and Justin Haynes (fiddle) who is also in IIIrd Tyme Out. Haynes was later replaced by Greg Luck.
- 2013, released first album called Session 1 (Mountain Fever Records.)
- 2013, Dilling announced his retirement from IIIrd Tyme Out, making Sideline his primary musical outlet.
- 2014, Webb and Luck left the band. Dilling decided to make Sideline a full-time band (rather than just a “sideline”) so he hired musicians (and brothers) Brian Aldridge (mandolin) and Nathan Aldridge (fiddle) later in the year.
- 2015 lineup: Dilling (banjo), Cherryholmes (guitar), Moore (bass), Brian Aldridge (mandolin), Nathan Aldridge (fiddle), Brad Hudson (reso guitar).
- 2015, released second album Session 2 (Mountain Fever).
- 2016, Brian Aldridge left the group. He was replaced by Troy Boone.
- 2017, Hudson left the group to pursue a solo career. Multi-instrumentalist and vocalist Bailey Coe joined.