The Face of a Winner

When Simon encourages Sydney to take the lead on an ad campaign for Windy City Coffee, disaster ensues. Meanwhile, Zach is jealous when Simon tasks Andrew with taking care of a family of ducklings.

When a client pitch shines a negative light on Simon and Sydney’s father-daughter relationship, Simon is determined to make up for all of Sydney’s bad childhood memories by re-teaching her how to drive. Meanwhile, Andrew’s confidence suffers when Lauren tells him that he is Zach’s suckerfish.

Instead of trying to come up with ideas for a breakfast burrito ad campaign, the gang procrastinates.

Sydney, Zach and Simon compete for the attention of a worldly client.

Sydney learns that her high school crush is nominated for a prestigious award -- in direct competition with her father.

A man (Josh Groban) who used to work with Sydney writes a song about her; Simon struggles with a pitch.

When a conflict arises, Simon and Sydney's partner (Brad Garrett) forces Simon to give up his very first client.

The annual accounts vs. creative 16-inch softball game puts someone's job on the line; the truth about Simon's last win may be revealed.

Gordon and Simon's values clash as they try to land a lucrative client; Lauren gets stuck in a $1 million bra.

When the bratty daughter (Ashley Tisdale) of an important client becomes the latest intern at Roberts and Roberts, Syndey's insecurities resurface.

After an account mix-up, Sydney becomes addicted to a video game.

When the rest of the office comes down with the flu, Simon lets Lauren work with a big client facing a PR disaster.

Andrew and Zach try to help Simon get his groove back following a creativity contest defeat; Sydney fears her new attachment to a cat will interfere with human relationships.

Simon is asked to eulogize a jingle writer who was not a well-liked man.

Simon offers to organize a bar mitzvah for a client's son, but things go south when Zach has a run-in with an ex.

A longing for grandchildren compels Simon to interfere with Sydney's new relationship; Andrew and Zach try working with different partners.

Andrew's spirited and rowdy sisters come to the office to celebrate St. Patrick's Day -- Simon's least favorite holiday.

While trying to channel Simon, Zach makes big promises during a pitch and must get Brad Paisley to sing a jingle written by Danny Chase.

Gordon and his partner break up, causing Simon to become disillusioned with love.

The team looks outside the box to try to prevent the closure of a library.

Simon's ex-wife has the final word when a corporation wants to buy out the firm.