Umphrey's McGee has played I Am Trying to Break Your Heart 1 time. It was first played on February 14, 2010 at Ram's Head Live!, Baltimore, MD, and last on February 14, 2010 at Ram's Head Live!, Baltimore, MD (1,494 shows since last played).
| Date | Venue |
|---|---|
| Feb 14, 2010 | Ram's Head Live!, Baltimore, MD |
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I Am Trying to Break Your Heart on All Things Umphrey's: every performance, jam notes and more.
Setlist data from All Things Umphrey's: allthings.umphreys.com. Updated October 21, 2026.