Harmony milk pirates
 

the large ones are 1961
Does any one know what year the small ones are from they are 4x5

Just a guess
 

The images on both are the same (just cropped differently). It is the same image used on the 1959 and the 1960 Jay publishing images. My guess would put it between 1959 and 1961.
How have you definitively dated the larger one to 1961?

Hoak played from 59 to 62 so those years are possible
I think lemke assumed since they won the world series in 60..appearances would be in 61

further thoughts
 

I am pretty sure the Pirates wore flannels in 1958 and moved to the vests in 1959. If accurate that would make 1959 the earliest possibility. I've confirmed the Pirates did appearances for Horne's department stores as early as 1958. Harmony Milk was a big sponsor/supporter of the Pirates. Most of the Harmony Milk player photos I've seen are autographed. The likelihood is they were from appearances. If you have the patience - you could try searching a newspaper archive of the Pittsburgh Press and Post Gazette looking for advertisements related to Harmony Milk sponsored appearances (That's what I did for Horne's a while ago). Based solely off the images my guess stands at 1959-1961 (thinking 1959-1960 more likely tied into the Jay photos).