The team finished the season with an 8–20 record – a far cry from their 26–14 record from 2018. A 3–2 victory over the Dallas Fuel in the final match of Stage 1 gave the Uprising a 4–3 record and qualified them for the Stage 1 Playoffs. However, they were eliminated in the quarterfinals after a 0–3 loss to the Vancouver Titans. Boston struggled to repeat the success they found in Stage 1, only winning four of their next fourteen matches before the implementation of an enforced 2-2-2 role lock by the league. The Uprising did not perform well under the new format, as a 0–4 loss to the Atlanta Reign on August 25 gave Boston a winless 0–7 Stage 4 record.
From August 1 to September 9, 2018, all Overwatch League teams that competed in the 2018 season could choose to extend their team's players' contracts. Uprising released four of their ten players – tied with Los Angeles Gladiators for the most in the league by a playoff team – in Shin "Kalios" Woo-yeol, Connor "Avast" Prince, Mikias "Snow" Yohannes, and Stanislav "Mistakes" Danilov.[1]
Boston's first offseason acquisition was on October 22, when Uprising signed DPS player Jeffrey "blasé" Tsang from Overwatch Contenders team Gladiators Legion.[2] On October 27, it was announced that flex support player Park "Neko" Seh-yeon had been signed to new expansion team Toronto Defiant.[3] The team promoted Kelsey "ColourHex" Birse and Minseob "Axxiom" Park from their academy team Toronto Esports three days later.[4] On November 4, Uprising signed main tank Cameron "Fusions" Bosworth, who had just recently competed in the 2018 Overwatch World Cup for team UK, on a two-way contract with Toronto Esports.[5][6] On December 3, Uprising transferred Kwon "Striker" Nam-joo to San Francisco Shock.[7] Two day later, the team signed Renan "alemao" Moretto, the first Brazilian player to sign to an Overwatch League roster.[8] The team's final offseason transaction occurred on February 12, two days before the beginning of the regular season, when Uprising transferred main tank Noh "Gamsu" Young-jin to Shanghai Dragons.[9]
Boston opened their season on February 14 with a match against the New York Excelsior; Boston lost the match 2–1 loss.[10] The Uprising's next match was against the Houston Outlaws three days later. Main tank Cameron "Fusions" Bosworth performed solidly in the match, as the team took a 3–2 victory.[11] The following week, Boston lost to the Shanghai Dragons by a 1–3 score, giving the Dragon's their first-ever franchise victory.[12] Boston clinched the sixth, and final, seed of the Stage 1 Playoffs.[13] The Uprising faced the top-seeded Vancouver Titans in the Stage 1 Quarterfinals on March 21. They did not win a single map against the Titans, losing the match 0–3.[14]
Two days prior to Boston's first match of Stage 2, the Uprising signed support player Zion "Persia" Yang, who had most recently played for Talon Esports of Overwatch Contenders Pacific.[15] On the same day, Boston traded flex tank Lucas "NotE" Meissner to the Dallas Fuel in exchange for flex tank Richard "rCk" Kanerva.[16] Boston failed to claim a Stage 2 playoff berth.[17]
In Stage 3, the Uprising went on a season-high 6-game losing streak, which was snapped on June 23 with a 3–2 win over the Paris Eternal.[18] The team ended Stage 3 with a 1–6 record.[19]
Prior to the start of Stage 4, which would debut the League's enforcement of a 2-2-2 role lock, the Uprising acquired DPS Lee "Stellar" Do-hyung, who had retired earlier in the season, from the Toronto Defiant.[20] The team did not fare well with the new change, losing all seven of their matches in Stage 4.[21]
