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Oldskool began his official competitive career with Gankstars Vega in Autumn qualifier 2 where he competed as a jungler with FooJee and R3cKeD. The team finished 3-4th in their first qualifier together and, with that, qualified for the Autumn Live Championships. At the Autumn finals, the team finished 3rd overall, beating VON Menace in the 3rd place match.
In the Winter Season, Vega stayed together. In Winter Qualifier 1, Vega lost to their sister team, Gankstars Sirius in the round of 8, Catherine Bracket finals. In qualifier 2, they lost in an upset to Rage Pingers, meaning that they did not qualify for the Winter Live Championships.
In the Spring Season, Oldskool left Vega and formed Nemesis Excrucio with Ezadox and iLoveJoseph. In their first tournament together, they finished 5-8th when they lost to Hammers Velocity in the Adagio bracket finals. In Spring Qualifier 2, they dropped affiliation with Nemesis and became just Excrucio and went on to finish 2nd after losing to Hammers Velocity in the finals. Shortly after the finish of qualifier 2, Excrucio was picked up by Team Phoenix and renamed to Phoenix Reign. At the Spring Live Championships, Reign finished 2nd overall, again losing to Hammers Velocity in the finals 3-1.
In the Summer Season, Oldskool remained on Reign with Ezadox and new additions e36 and Statusbaked. . When Ezadox retired, Status's brother, Sam, took over as starting Roam. During this time, Skool became known in the community for his exceptional Celeste play. Reign finished Evil Eight Split 2 in second place, giving them the second seed going into the Summer Live championships.