The first press box at Fenway Park was built in 1933 by Tom Yawkey in his major renovations to the park. This press box, behind home plate, was much smaller than the current press box. It was still the top level of the ballpark in the 1930s, hovering just above the grandstands.

The press box lasted until 1989, when it was completely gutted and replaced with the current press box, with an additional premium seating club beneath it.