These photos likely look awfully familiar to you, and that's because the demolition of the 1937-built Wrigley Field bleachers back in 2005 was a similar operation to the current demolition project.
There are photos in this gallery taken both by David Sameshima and by me; the photos I took (the first nine in the gallery) should be dated October 13, 2005 (please ignore the "1/6/2000" date stamp on the photos -- obviously, something was wrong with the date function on my camera). David's were taken October 15, 2005 (pictures 10-13) and October 23, 2005 (pictures 14-22).
One of the things that was different nine years ago is that the scale of the project was smaller -- Waveland and Sheffield weren't entirely closed so you could get quite a bit closer to the "action," and many times, as you can see, the construction fences were open so we could get a real good closeup look at what was going on.
This series on the demolition of the original bleachers and construction of the bleachers that are currently being demolished will continue on an occasional basis this offseason.