|In the study group's third year together at Greendale, Shirley and Pierce form a business partnership and submit a proposal to Dean Pelton to open an eatery named Shirley's Sandwiches. It was to be located where the coffee shop "Hot & Brown" used to be before it was burned down. Although at first rejected in favor of a Subway franchise, the proposal is eventually accepted and Shirley and Pierce have a grand opening during the summer time for the shop. Its first appearance was in the Season Three episode "Introduction to Finality".|
After her husband, Andre Bennett, left Shirley and his family, she decided to go back to Community College. She took classes which would help her in her goal to one day start her own business based on her culinary skills. In their junior year at Greendale, Britta saw an opportunity for Shirley to make her dreams come true and suggested that she open a sandwich shop where the "Hot & Brown" coffee shop once stood. Pierce had been looking to invest his money in new business ventures and offered to help bankroll Shirley in this new enterprise. Shirley was reluctant at first as she wanted to focus on her upcoming nuptials to Andre, who had recently just proposed that they get married again. Britta decided to plan the wedding while Shirley puts her efforts into submitting a business proposal for Dean Pelton to consider.
Pierce is overly enthusiastic about the sandwich shop idea but Shirley is unimpressed with the presentation he came up with. She is about to quit the venture altogether until Pierce admits that he was let go as the C.E.O. of Hawthorne Wipes by it's board of directors. He sees the sandwich shop as a shot at finally being somebody and pleads with Shirley to let him invest in her as he has all the money but none of the good ideas to go with it. Shirley reconsiders and puts her energies into reworking the business proposal. Later in Dean Pelton's office, Shirley and Pierce present their sandwich shop plans to the dean and conclude the presentation in the cafeteria. Greatly impressed with their presentation, Dean agrees to their proposal.
Afterwards, Dean Pelton delivers some unfortunate news to Shirley and tells her that the Greendale broad of directors decided to go with a Subway franchise instead of her sandwich shop. A few weeks later, the Subway restaurant opened in the cafeteria as a disappointed Shirley and Pierce looked on. Resolving to somehow shut it down, they decide to take down the Subway representative who just enrolled in the school. Enlisting Britta to help them, they manage to get audio footage of the two of them together in flagrante delicto. Presenting this evidence to the representative's superior, they get him fired, but their plan proves unsuccessful when he is simply replaced with someone else. It's only after a riot breaks out in the cafeteria and the restaurant is destroyed in the chaos does that franchise finally shut down.
During the summertime, Dean Pelton lets Pierce and Shirley know that their sandwich shop idea has finally been approved by the board. However, when he gives them a form to sign it requires only one signature and acknowledges only one of them as sole owner of the shop. Shirley and Pierce start to argue as to who deserves that honor which leads to a showdown between the two in a makeshift Greendale courtroom. Pierce is represented by Alan Conner while Shirley is represented by Jeff. After Alan tries to blackmail Jeff into tanking the case, Shirley inspires him to do the right thing. He delivers his closing arguments with a stirring speech on friendship and selflessness. Moved by his words, Pierce fires Alan and drops his case against Shirley. He then proposes that Jeff sign the form for them and act as their representative which Shirley happily agrees to. Not long after, Shirley's Sandwiches finally launches with much fanfare in the cafeteria.
In the study group's senior year at Greendale, Abed and Pierce sit at one of sandwich shop tables and watch the "Hunger Deans" competition unfold in the cafeteria ("History 101"). Later, Shirley is seen wearing a sandwich shop uniform, a green polo shirt with the SS logo on it, when the study group faces a protest against them led by The Germans ("Alternative History of the German Invasion"). Some time later, Ben Chang returns to the campus several months after his reign of terror over Greendale claiming to have amnesia, Shirley believes him and hires him to work at the sandwich shop and defends her decision to Jeff who believes Chang is faking. Shirley says everyone deserves a second chance and also adds that he is a good worker who is great with the customers ("Advanced Documentary Filmmaking").
The day before Jeff's graduation that year, he has a daydream featuring the sandwich shop. In this dream his evil twin from The Darkest Timeline is invading this world. He imagines that Troy and Shirley are at the sandwich shop working on a mobile breakfast sandwich cart. Evil Jeff stopped by to uninvite them to Jeff's graduation ceremony. He mocked Shirley for spending too much time on her business and ignoring her family. He also told Troy his idea of a "Troy-jan Horse" sandwich was stupid because people would assume there was horse meat in it. The Evil Study Group hunts down their counterparts in the cafeteria. As the two groups clash, Annie at first hides from her double in the sandwich shop. However, after being taunted by Evil Annie , Annie emerges from her hiding place and shoots her double with a Darkest Timeline paintball gun, sending her back to her world ("Advanced Introduction to Finality").
After graduating from Greendale, Shirley unsuccessfully tried to expand her business and lost a substantial amount of her family's money in the investment. Her shop at Greendale had been shut down because of this and was sealed off with hazard tape and an "Out of Business" sign ("Repilot"). Shirley somehow managed to rebound and not long after re-enrolling at Greendale got the shop running again. A grand re-opening ceremony was held where she cut a ceremonial ribbon and introduced a newly renovated shop. For the ceremony she had her sons Elijah and Jordan sing the song "Creep". The performance was cut short when Garrett interrupted and proclaimed the return of the "Ass Crack Bandit". Due to the assailant's modus operandi, all coins on campus were outlawed for a time. Shirley's sandwiches made a significant profit because of this by rounding all their prices up ("Basic Intergluteal Numismatics").
Before the 2015 semester was to start at Greendale, Shirley's father became sick and she had to go to Florida to take care of him. She left her sandwich shop in Britta and her old study group's care. Unfortunately, Britta was far less skillful in the kitchen than Shirley and customers like Dave complained about their food being poorly cooked. When the Save Greendale Committee fails to avert a disaster, the school hires a consultant named Frankie Dart. She imposes a zero tolerance rule against alcohol on school grounds which inspires Jeff to hatch a crazy scheme involving the sandwich shop. Using the shop as a front, he Britta and Annie open a secret speakeasy ("Ladders").