| OH BOY | August 5, 2003 | Verizon Wireless Amphitheater (Noblesville) | Performed with The Dead rather than Dylan's own band. Dylan originally rehearsed this song with the Grateful Dead in spring 1987. |
| OLD MacDONALD HAD A FARM | September 5, 1990 | Zoo (Oklahoma City) | Performed only as an instrumental opener. |
| OLD MAN | October 8, 2002 | Memorial Auditorium (Sacramento) |
| OLD ROCK AND ROLLER | July 3, 1990 | Stadtpark (Hamburg) |
| OMIE WISE | probably spring 1960 | |
| Reported as a regular feature of Dylan's St. Paul club sets. The earliest recorded live performance comes from the July 29, 1961 Riverside Church broadcast. | ||
| ONE IRISH ROVER | July 1, 1989 | Civic Center Arena (Peoria) | Dylan also backed Van Morrison on this song for the BBC documentary "One Irish Rover," filmed in Athens, Greece only a few days earlier, June 28. |
| ONLY THE LONELY | February 24, 1990 | Universal Amphitheater (Los Angeles) |
| Song performed by an ensemble including Dylan at a Roy Orbison tribute. | ||