| Date | Venue | City | State | Country | Artist |
|---|---|---|---|---|---|
| 1999-12-18 | Magoo's Underground Lounge | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-12-04 | Brother Jimmy's | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-10-30 | Martyrs' | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-09-24 | Subterranean | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-09-02 | Gameworks | Schaumburg | Illinois | USA | Umphrey's McGee |
| 1999-08-20 | Martyrs' | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-07-17 | Elbo Room | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-06-11 | Elbo Room | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-05-29 | Martyrs' | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-05-23 | Schubas Tavern | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-05-20 | Elbo Room | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-04-17 | Martyrs' | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-04-02 | Elbo Room | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-03-19 | Schubas Tavern | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-02-26 | Martyrs' | Chicago | Illinois | USA | Umphrey's McGee |
| 1999-01-23 | Elbo Room | Chicago | Illinois | USA | Umphrey's McGee |