Oscar Brennan

Oscar played for Bray Wanderers u19 squad for the 2014/15 season. He left at the end of the season and moved to UCD's u19 squad for the 2015 short season but was soon on the move once again as he signed for Cabinteely ahead of the 2016 First Division campaign. He made his league debut in a 2-1 win over Athlone Town at Stradbrook on 4 March 2016 and scored once during the campaign, in a 5-1 win over Athlone Town. Oscar made 26 league appearances that year but left the club at the end of the season.

In December 2016 Oscar signed for Keith Long at Bohemians ahead of their 2017 Premier Division campaign. He spent two years at Dalymount Park but in November 2018, Oscar signed with First Division side Shelbourne for the 2019 campaign. Having made 10 appearances during the Covid hit 2020 season, Oscar departed Shels following their relegation to the First Division.

In February 2021, Oscar signed for Waterford and spent one year with the Blues. Waterford were relegated that season and in December 2021 Oscar agreed to join Bray Wanderers for the 2022 season. However, a few days before the season began Oscar joined Leinster Senior League side, Crumlin United.