| 19/05/2019 | Sun | Rehearsal | 7pm | Royal Oak | Green Lane Ockbrook | Big Band | Private |
| 26/05/2019 | Sun | Bank Holiday / No Concert | | | | | |
| 02/06/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 09/06/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 16/06/2019 | Sun | Rehearsal | 7pm | Royal Oak | Green Lane Ockbrook | Big Band | Private |
| 23/06/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 29/06/2019 | Sat afternoon | 70th Wedding Anniversary | AfternoonTBC | Rolleston Club | Rolleston Club | OBB 8 | Private |
| 30/06/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 06/07/2019 | Sat | Concert | 7 - 9.20pm | Spondon Methodist Church | Lodge Ln, Derby DE21 7GF | Big Band / OBB16 / Two Vocalists | Public / Ticketed |
| 07/07/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 14/07/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 21/07/2019 | Sun | Rehearsal | 7pm | Royal Oak | Green Lane Ockbrook | Big Band | Private |
| 27/07/2019 | Sat | Outside Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 17/08/2019 | Sat | 1940s Themed Dance | 8 - 11pm | Osgathorpe Hall | Osgathorpe Hall, Church Lane, Osgathorpe, Loughborough LE12 9SY | Big Band / OBB 16 / Two vocalists | Private |
| 01/09/19 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 07/09/2019 | Sat | Dinner Dance | TBA | Victory Show | The Victory Show, Foxlands Farm, Cosby, Leicestershire, LE9 1SG | Big Band | Refer to Event Website |
| 08/09/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 15/09/2019 | Sun | Rehearsal | 7pm | Royal Oak | Green Lane Ockbrook | Big Band | Private |
| 22/09/2019 | Sun | Dance / Small Band (TBC) | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Small Band | Public / Free Admission / Raffle |
| 29/09/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 06/10/2019 | Sun | Concert | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Big Band | Public / Free Admission / Raffle |
| 13/10/2019 | Sun | No Concert / Royal Oak Beer Festival | | | | | |
| 19/10/2019 | Sat | Gala Dinner | 8 - 10pm | Novotel | Bostocks Ln, Long Eaton, Sandiacre, Nottingham NG10 4EP | OBB13 | Private |
| 2/11/2019 | Sat | Birthday Dance | 8.30 - 9.30pm | Moira Village Hall | Ashby Rd, Moira, Swadlincote DE12 6DZ | OBB 12 (Female Vocalist) | Private |
| 24/11/2019 | Sun | Dance | 8 - 10pm | Royal Oak | Green Lane Ockbrook | Small Band | Public / Free Admission / Raffle |
| 22/12/2019 | Sun | Christmas Dance | 8 - 10.30 | Nunsfield House | Nunsfield House Alvaston Derby | Big Band | Public / Admission Charge / Raffle |