Traditional applique was often very stylized with shorthand indications of florals. The eight-lobed flat flower with a circle in the center is the classic 19th-century applique. Circles or dots usually stood for a fruit as in the bowl here.
Estimated date 1840-1880
Here we have fruit in the border and flowers with five-lobed florals in the inner wreath.
The imagery in 19th-century applique has a lot to do with Pennsylvania-German folkarts.
Where flowers are similar
Here's a painting dated 1835
And one from 1825 with four-lobed flowers.
Pieced quilt with an appliqued border
Estimated date 1840-1860
from Laura Fisher Antique Quilts
We see these flowers used in many ways by quilters.
Estimated date: 1850-1900
Collection: Minneapolis Institute of Arts
I looked through files of applique quilts and didn't notice any significant groups of flowers made just from circles. Circles seem to stand for fruit as in the tree above or maybe buds.
Here's an 1849 New York sampler from an online auction with a few simple trees.
Sara Keplar 1851
Collection: Colonial Williamsburg
Notice the fruit trees in the border.
When Karla and I were looking for inspiration for our Juniper and Mistletoe sampler we found most of the trees in mid-19th-century borders.
The idea of plain circles or concentric circles as flowers does not seem to be a 19th-century idea. I looked through my Encyclopedia of Applique and didn't find any lollipop flowers from old samplers or 19th-century newspaper patterns.
But in the 20th century, pattern designers started simplifying the basic flat floral, creating lollipop flowers.
See a post with more about this quilt kit and the ditsy flower here:
This pattern is not in the Encyclopedia of Applique and I don't know the designer. But I did find several other lollipop flowers designed in the 1930s. I took some bad snapshots of the sketches in the index.
Geranium from the Aunt Martha company in the 1930s
On the page of Miscellaneous Bouquets are several from the Chicago Tribune's quilt columnist in the 1930s Nancy Cabot. Her real name was Loretta Leitner and she did a lot of modernized designs---most of which nobody ever made.
But it's not too late.
Certainly lollipop flowers are hot today. Do a websearch for the terms:
lollipop flower quilt
And see what comes up.
Here are two I found:
So the short answer to the question: What is the history of lollipop flowers? It's a short history and we are right in the middle of it now.