[3] Villa surrendered a two-goal lead, drawing 3–3 at home to bottom club Preston North End on 2 October 2018.

[8] He immediately managed to reinvigorate the "Villans" attack, and only a controversial injury-time equaliser from local rivals West Bromwich Albion at The Hawthorns denied them a place in the play-offs by 7 December.

[9][10] However Villa's form dipped dramatically in the three months after Jack Grealish was sidelined with a shin injury picked up in that match, but on 2 March, Smith gave Grealish the captaincy on his return to the first-team and the 23-year old inspired an important 4–0 victory over play-off rivals Derby County and went on to captain the team from that game onwards.

On 22 April 2019, the team surpassed a 109 year old club record for longest winning run after defeating Millwall 1–0 at Villa Park to make it 10 successive victories in 10 matches.

[16] On 11 May, the new manager oversaw his 18th win with Aston Villa as they came from behind to beat West Brom 2–1 in the first leg of the Championship play-off semi-finals.

[24][25] The third round draw was made live on BBC by Ruud Gullit and Paul Ince from Stamford Bridge on 3 December 2018.