Although claiming a foundation date of 1875,[1] the club does not appear to have been particularly active, until entering the Cheshire Senior Cup in 1883, losing in the first round to Macclesfield St John's.

The club was let down by its finishing; Bollington "had the best of the play, but weak shooting rendered every run useless,showing the great contrast to Oswestry, who seldom missed a good chance".

[4] Undaunted, the club entered again the 1886-87, receiving the same draw; this time Bollington moved the tie to Macclesfield, being rewarded with a crowd of 700, but Oswestry won 8–2, scoring in the second minute and, like the previous year, being 4–0 up at the break.

[5] Bollington also exited the Cheshire Cup at the second round for the second consecutive year,[6] although the club played for 80 minutes with ten men after outside-left winger Arden had his eye infected by lime from the boundary lines when the ball was kicked in his face.

[8] However the gap between Bollington and the top clubs in the county was shown by their first round exit in the Cheshire Cup in 1888–89 to Crewe Alexandra by nine goals to two.