[6] He then moved to Livingston, playing for the under-19s before progressing to the first team and making his debut on 26 April 2008, as a substitute in a 5–2 defeat against St Johnstone.

[7][8] In March 2009, Halliday alongside then Livingston teammates Leigh Griffiths and Joe McKee spent five days on trial with Italian Serie B side Parma.

On 28 December, Halliday received a straight red card in Rangers' 4–2 win over Hibernian by referee Bobby Madden for violent conduct after clashing with Hibs' midfielder Fraser Fyvie.

On 25 January, Halliday was sent off for the second time that season in controversial circumstances during a league match away to Morton: he was alleged to have made an offensive gesture to the home support after Barrie McKay had scored to make it 2–0 to Rangers which led him being shown a second yellow card,[29] and the decision by referee Barry Cook angered both player and Rangers manager Mark Warburton.

[34] The following season, Halliday made his Scottish Premiership debut in August 2016, starting in midfield in a 1–1 draw against Hamilton Academical.

[38] Halliday's appearances became less frequent under new manager Pedro Caixinha,[10] and Rangers finished the season in third place behind Aberdeen and Celtic.

He was named in the starting line-up in the semi-final of the 2017–18 Scottish Cup against Celtic, but was substituted for Josh Windass before half time with Rangers already two goals behind; Halliday was caught by television cameras shouting to the crowd showing his frustration at the situation.

Under new manager Steven Gerrard in 2018–19, Halliday's involvement increased as the campaign progressed, playing either at full-back or midfield including seven appearances in the Europa League.

[10] In an important league meeting with Celtic at Ibrox on 29 December 2018, he put in a committed performance in a 1–0 Rangers win,[46] with Gerrard praising him as 'my unofficial captain'.

[49] On 19 January 2024, Halliday joined fellow Scottish Premiership club Motherwell on loan until the end of the season, which would turn into a permanent deal in the summer of 2024.

[51] He travelled to Manchester in 2008, when Rangers played in the UEFA Cup Final against Zenit Saint Petersburg, missing a school exam in the process.