Three times for me.
#1 Late February 2001 -- Grand Rapids, MI (Matthew Good Band)
Was front row left, was at a really small place, believe it was called the Intersection, met the entire band after and got all their autographs/pics
One of the best nights of my life.
#2 March 17, 2008 -- Chicago, IL (just Matt acoustically)
Was front row center, got the set list, met Matt after, got a picture with him and had him autograph the setlist.
Again one of the best nights of my life.
#3 Late June 2008 -- Vancouver (Matthew Good and his band)
Not front row this time but still a great concert, did not try to meet him after
Was a special concert to me on this night. I was on vacation with my girlfriend and I found out my Grandpa passed away that morning.
Hopefully he will come to the US in 2010 and I can make it number 4.