2018–19 Scottish Challenge Cup

The 2018–19 Scottish Challenge Cup, known as the IRN-BRU Cup due to sponsorship reasons, is the 28th season of the competition. The tournament takes on a similar format from the previous season with the addition of two teams from England's National League entering the competition for the first time. This will take the total number of participating clubs to 58.

Thirty teams from the Scottish Championship, Scottish League One and Scottish League Two will compete, along with four teams from the Highland Football League (one eliminated in preliminary round) and four from the Lowland Football League (one eliminated in preliminary round). In addition to this, the Under-20 teams of the teams competing in the Scottish Premiership will be represented. This will be the third edition with two clubs from both Northern Ireland's NIFL Premiership and the Welsh Premier League and will be the second time that two teams from the League of Ireland will enter. The Welsh teams are The New Saints and Connah's Quay Nomads while the Northern Irish teams are Crusaders and Coleraine. The teams from the Republic of Ireland are Bohemians and Limerick. Sutton United and Boreham Wood will represent England's National League.

Inverness Caledonian Thistle are the defending champions after they beat Dumbarton 1–0 in the 2018 final.

First round
The draw for the first round was made on 26 June 2018 at 1pm live on SPFL Facebook page.

Broadcasting rights
The domestic broadcasting rights for the competition are held jointly by BBC Alba, S4C](for matches involving Welsh teams) and subscription channel Premier Sports. Prior to the re-format in the 2016–17 season, BBC Alba had exclusive rights.