Being the vice captain, he has a soothing and gentle personality for his teammates and acts as a pillar of support for them. Even though he isn't Karasuno's regular setter anymore, he does not dream of giving up on playing. As such, he encourages himself and all of his teammates to never give up, no matter how rough the situation might be.
Coming from Nagamushi Junior High, Sugawara joined the volleyball club during his first-year with Daichi and Asahi.The three of them were excited to join Karasuno, a school that performed well in the recent nationals. However, they quickly found that reality differed from their expectations. The club lacked a proper coach and couldn't organize practice matches due to their lackluster performances. Everything seems lost until the first-years decided to do extra practice under Daichi's leadership. The team made some progress and became fired up to go to nationals once again. The first-years were particularly excited when the Miyagi Prefecture's Interhigh Qualifiers began, but they were quickly disappointed when Karasuno got knocked out early in the second round. Later, Sugawara, Daichi, and Asahi listened to their previous captain, Tashiro telling them to take advantage of any chances that arose.
Sugawara goes with Daichi and Tanaka to the junior high tournament to watch the "King of the Upper Court". A year later, Sugawara enters the Karasuno gymnasium alongside Daichi and Tanaka to greet the new members of the club—the same players they'd watched in the tournament.Sugawara approaches Kageyama and remarks that he's grown taller. Suddenly, Tanaka points out Hinata as the shorty from last year, surprising Sugawara. The third-year compliments Hinata for his jumps and encourages Hinata's goal of becoming the ace. However, Kageyama quickly criticizes Hinata for it, leading to a small fight that gains the vice principal's attention. Sugawara and Daichi try to show the vice principal that nothing's going on, but to no avail as the two first years challenge each other to a mini-match.