Win Draw Loss Postponed Hearts returned for pre-season training on 21 June,[3] with the first preseason friendly scheduled to take place against Arbroath at the start of July.

[3] During the winter break Hearts travelled to Murcia for a five-day training camp, playing a bounce game against Lokeren.

[17] On 25 May, Hearts were drawn in Group C, alongside Cove Rangers, Cowdenbeath, Inverness Caledonian Thistle and Raith Rovers.

[22] Irving's contract extension had not been correctly lodged with the Scottish Football Association, rendering him ineligible to play as his registration expired on 9 June.

Kevin Nisbet opened the scoring early in the second half for the home side, before Michael Smith equalised from 25 yards out.

[28] In the 90th minute Christophe Berra had a goal disallowed for impeding the keeper, however replays showed the foul was committed by a fellow Raith player.

A goal in the second half from Aidan Keena secured the 4–0 win but not before an injury forced them down to ten men for the final twelve minutes.

[44] The replay at Tyncastle Park saw the away team getting the opening goal in the 17th minute from a Scott McDonald tap to give the championship side the early lead.

Sean Clarke gave Hearts a 3–0 victory after Ikpeazu was brought down by Mark Ridgers to give a penalty which was converted.

[54] Naismith's stint as Captain lasted just three games, as he suffered a tear in the cartilage in his knee during the League Cup Semi-final and was ruled out for a period of six to eight weeks.

In addition striker Steven MacLean accepted a retrospective two match ban for violent conduct against Celtic's Eboue Kouassi in the League Cup.

[61] A yellow card issued for simulation to Uche Ikpeazu during the game versus Aberdeen on 30 March 2019, was rescinded on appeal.

Former vice chairman and director Pilmar Smith,[98] 1956 Scottish Cup club captain Freddie Glidden[99][100] and defender Tommy Darling,[101] Over the course of the season a number of the Hearts squad were called up on international duty.

[116] The interactive play A War of Two Halves was presented at Tynecastle, dealing with the stories of the original 13 players who joined the 16th (Service) Battalion of the Royal Scots.