Massey has made all 14 of his appearances in European competition for Dundalk and was part of their team that became the first Irish side to reach the play-off round of the UEFA Champions League in August 2016.

[1] Massey grew up in the Knocklyon suburb of Dublin[2] and played youth football for Cherry Orchard in the same team as Simon Madden, Adam Rooney and Stephen Gleeson.

He made his professional debut in a League of Ireland Cup tie against Shamrock Rovers in May 2008 and went on to play five times that season for the club.

[5] He cited Kenny's pledge to utilise him in an attacking full-back role, as opposed to the more defensive game he played at Bray, as being one of the deciding factors for the move.

He played in all 33 league games, scoring two further goals in wins over Sligo Rovers and UCD, as Dundalk won the Premier Division title.

In 2015, Massey went on to make 32 league appearances for the club, scoring four goals in the process, as Dundalk once more won the Premier Division title.

In April 2015, his form led to calls in the media for his inclusion in the Republic of Ireland national team and manager Martin O'Neill indicated that he would be following Massey's performances closely.

[11] In 2016, Massey played every minute of all 6 of Dundalk's UEFA Champions League qualifier games as they became the first ever Irish side to reach the play-off round.

[14] He started all 5 of Dundalk's European matches, although their campaign ended prematurely when they were beaten twice over 2 legs by Rosenborg in the UEFA Champions League qualifiers.

[15] He made 37 appearances in all competitions Massey was named as club captain ahead of the 2018 season, and wore the armband for all of Dundalk's opening 11 league matches.

[16] His goal in a 5-2 thrashing of rivals Shamrock Rovers at Tallaght Stadium also proved crucial when Dundalk sealed the league title once again.

[22] On 8 January 2021, just 24 hours after leaving Dundalk, Dane Massey signed a one-year contract with their local rivals, newly promoted Drogheda United.

His first goals in his new colours came in the reverse fixture, a 7-0 thrashing of Waterford's U19 side who had been fielded due to a COVID 19 outbreak in the senior squad, on 8 May.

Massey made his second debut for Bray, captaining the side to a 1–0 win away to Treaty United on the opening day of the 2023 First Division season.

[5][7] In 2014, Massey balanced training and matchday commitments at Dundalk with working a few mornings a week as an electrician in the Jervis Shopping Centre in Dublin,[6] however he gave this up at the beginning of 2015 to go full-time.