The year's touring kicked off in Clearwater, FL on March 3 and concluded in Sarnia, ON on November 27.  The Alexandria, VA; Santa Barbara, CA and Bayfield, WI dates were actually double performances with two separate one set concerts with a new audience for each show.

The most interesting addition to the setlists was the occasional inclusion of Forgive Me Lord and Heaven Don't Deserve Me, two out-takes included on Songbook, making it ointo a number of shows. I'll Do Anything, with an updated bridge, was another pleasant surprise, as was That Same Old Obsession. Red Velvet was introduced for the western Canadian shows as Ian Tyson was expected to attend the Calgary show. Shadows also returned after not appearing in 1998. Songs dropped from last year were Sit Down Young Stranger and On Susan's Floor. There were  fewer albums shut out entirely this year.  Only Back Here On Earth and Salute failed to have a song registered in 1999.  Endless Wire only just made it however, as the title song was played one time on the first night of the year's shows! There were 55 different songs performed during the year. No new or previously unreleased songs were played this year.

14 Karat Gold agained opened the majority of concerts, continuing the pattern from the fall of 1996 when it first was used to open the shows, but it was replaced as opener late in the tour but reinstated for the last concert of the year in Sarnia. The encores were somewhat varied this year.  Long time favorite, Old Dan's Records only closed the show once, with a variety of others such as, Cold On The Shoulder; Blackberry Wine; Restless; Baby Step Back; Early Morning Rain; Pussywillows Cat-Tails; Rainy Day People; Canadian Railroad Trilogy and even In My Fashion being employed on any given night.