In the early 1960s, Trench used a dye cutter to remove the rectangular portion of the picture window. They made so many photo pennants, this machine was a worthwhile investment. As Greg noted, they typically used a photo printed on a cardstock-like paper that was affixed to the back with a pre-cut, rectangular clear tape. Additionally, their photos were, at least in the early 1960s, printed exclusively for their use; and bore their name and/or Sportservice's name on the reverse, along with a team roster/caption.
After 1962, Trench's photo backs no longer bore their name. By the 1970s, they occasionally used post cards, supplied by other vendors, for the photo.
Other manufacturers of course dabbled in photo pennants in the 1960s. ASCO's photos often came from post cards, supplied by other vendors. WGN made a few photo pennants as well; however, they got a bit lazy: they just stapled the photo to the pennant's front-side, thereby bypassing any need to cut the window or tape the pennant. And at least one maker actually screen printed the image of the team photo on to the felt, using half-tones--a printing technique actually pioneered by The Reproduction Co. back in the 1910s. See, e.g., this 1960 NL champs pennant....
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