[4] On 15 December 2019, Masouras scored a brace, converting two right-wing crosses from Hillal Soudani in a 5–0 win against Asteras Tripolis at the Theodoros Kolokotronis Stadium.

The 25-year-old then registered his second goal just two minutes later, successfully connecting with Hillal Soudani’s pass to beat the goalkeeper with ease in a 4–1 home win game against AEL.

[8] On 18 September 2020, in the 2020–21 Super League Greece opener game, the entry of Masouras in the beginning of the second half, scorer of two goals, changed the image of the match and Olympiacos started the championship with a 3–0 home win against Asteras Tripolis.

[12][13] On 30 September 2021, in a UEFA Europa League group stage, Giorgos Masouras made the difference by scoring twice (63 ′, 68 ′), while he also gave an assist to Tiquinho's goal, to help his team seal an emphatic 3–0 away win against Fenerbahçe.

[15] On 9 February 2022, Masouras with a goal at the last minute of the game and with another in extra time sealed the qualification in the semifinals of the 2021–22 Greek Football Cup against Panetolikos He was voted man of the match for his performance.

[18] In his second appearance with Bochum, the Greek midfielder scored his first two goals in Germany within an explosive two minutes and single-handedly led his team to a 2-0 win against Borussia Dortmund.