*Club domestic league appearances and goals, correct as of 21:53, 3 June 2024 (UTC) ‡ National team caps and goals, correct as of 23:59, 15 January 2024 (UTC)
Bolger made his senior debut for UCD in a 1–0 loss to Cork City on 23 March 2007.[2] His first goal at senior level came on 22 August 2008 in a 2–1 loss to Derry City at the UCD Bowl.[3] Following their relegation in 2008, Bolger was part of the UCD side that won the 2009 League of Ireland First Division title to regain promotion.[4] He impressed upon the club's return to the League of Ireland Premier Division, scoring 7 goals in 33 appearances in all competitions. In total he made 76 appearances in his 4 seasons with the club, scoring 10 goals.
Sporting Fingal
Bolger signed for Sporting Fingal ahead of the 2011 season, but on 9 February 2011 the club went bust, cancelling all player contracts in the process, in Bolger's case before he had even made his debut.[5]
Dundalk
On 10 February 2011, Bolger signed for Dundalk.[6] He made his debut 4 days later in a 5–3 win away to Linfield in the Setanta Sports Cup.[7] On 14 May 2011, he featured in the Final of the 2011 Setanta Sports Cup, as his side were defeated 2–0 by Shamrock Rovers at Tallaght Stadium.[8] He scored his first 2 goals for the club in a 6–1 win over Galway United on 24 June 2011.[9] Bolger made a total of 33 appearances during the season, scoring 2 goals as the side finished in 7th place.[10]
On 13 October 2013, Bolger opened the scoring with a 25-yard strike into the top corner in a 2–0 win over Sligo Rovers at Richmond Park, a win that secured the 2013 League of Ireland Premier Division title for the club.[15] On 20 October, 2 days after being award the league trophy, Bolger featured in a fatigued Pats side that were defeated 1–0 by Shamrock Rovers in the 2013 Leinster Senior Cup Final.[16] He was named in the PFAI Team of the Year for 2013 by his fellow players on 17 October 2013.[17] On 17 November 2013, Bolger was named as the club's Player of the Year by their supporters.[18]
On 18 February 2017, he was part of the team that defeated Dundalk 3–0 in the 2017 President of Ireland's Cup to retain the trophy.[32] On 12 June 2017, he was part of the side that won the 2017 Munster Senior Cup with a 4–2 win over Wilton in the final.[33] Bolger claimed the second Premier Division medal of his career on 17 October 2017, when Cork clinched the 2017 League of Ireland Premier Division title following a 0–0 draw with Derry City.[34] On 5 November 2017, he helped his side complete the double by defeating Dundalk 5–3 on penalties in the 2017 FAI Cup Final following a 1–1 draw after extra time, with Bolger scoring his penalty in the shootout.[35]
Shamrock Rovers
On 7 November 2017, Bolger agreed to join Shamrock Rovers for their 2018 season.[36] He made his debut for the club on 16 February 2018 in a 3–1 defeat to Bohemians at Dalymount Park.[37] On 14 September 2018, he scored his first goal for the club in a 5–0 win over Limerick at Tallaght Stadium.[38] On 3 November 2019, Bolger scored his penalty in the shootout as his side defeated Dundalk 4–2 on penalties in the 2019 FAI Cup Final following a 1–1 draw after extra time, ending a 32-year wait for an FAI Cup win for his club.[39] Bolger picked up an injury in a friendly with Wexford in July 2020 that would rule him out until late in the season.[40] He recovered from injury in time to play a part in the 2020 FAI Cup Final, replacing Dylan Watts in the 83rd minute as his side were defeated 4–2 by Dundalk after extra time in a behind-closed-doors Aviva Stadium.[41]
Sligo Rovers
On 11 December 2020, it was announced that Bolger would be signing for Sligo Rovers ahead of the 2021 season, reuniting with Liam Buckley, his former manager at St Patrick's Athletic.[42][43] He was named League of Ireland Player of the Month for the second time in his career for the month of May 2021, after leading his side to the top of the table.[44] Bolger signed a new contract with the club on 17 November 2022 that would see him act as a player-coach under manager John Russell, who was a former teammate of Bolger's at St Patrick's Athletic.[45] On 29 April 2023, Bolger scored his first and only goal for the club in a 2–1 defeated to his former club Shamrock Rovers.[46] He made a total of 88 appearances in all competitions for the club, scoring 1 goal.[10]
Bolger was called up to the Republic of Ireland U23 side for their game against England in May 2010,[50] making his debut in a 2–1 loss.[51] He also featured in the side's 1–0 win away to Estonia in September 2010.[52]