2023–24 Scottish Challenge Cup

The 2023–24 Scottish Challenge Cup, known as the SPFL Trust Trophy due to sponsorship reasons, was the 32nd season of the competition. The total number of participating clubs was 53, including clubs from Wales and Northern Ireland. The competition began on 1 August 2023 with the first round and the final took place on 24 March 2024.

Thirty teams from the Championship, League One and League Two competed, along with four teams from the Highland Football League and four from the Lowland Football League. In addition to this, Under-21 teams from 11 of the 12 clubs competing in the Scottish Premiership were represented. This season also included guest clubs, with two sides each coming from Northern Ireland's NIFL Premiership (Cliftonville and Coleraine) and the Welsh Cymru Premier (TNS and Bala Town).

First round
The first round featured 3 clubs from 2022 to 2023 Scottish League Two, 4 clubs from the 2022–23 Scottish Highland Football League, 4 clubs from the 2022–23 Scottish Lowland Football League and 11 of the 12 under-21 teams of the 2023–24 Scottish Premiership, with Ross County not entering an under-21 team.

The draw was made on 4 July 2023 at 13:00 and broadcast live on the SPFL YouTube Channel. The draw was regionalised and all non-Under 21 teams were seeded. The matches were played on 1 and 2 August 2023.

Draw
Teams that entered the competition in the first round.

Draw
Teams that entered the competition in the first round.

Second round
The second round featured the 11 winners from the previous round, along with 2 clubs from 2022 to 2023 Scottish League One and 7 clubs from 2022 to 2023 Scottish League Two.

The draw for the second round was also made on 4 July 2023 at 13:00 on the live broadcast from the SPFL YouTube Channel. The draw was regionalised, but not seeded. The matches were played on 15 and 16 August 2023.

Draw
Teams that entered the competition in the second round.

Draw
Teams that entered the competition in the second round.

Third round
The third round featured the 10 winners from the previous round, along with the bottom club from 2022 to 2023 Scottish Premiership, 2nd-10th from 2022 to 2023 Scottish Championship, 8 clubs from 2022 to 2023 Scottish League One, 2 clubs from 2022 to 2023 NIFL Premiership and 2 clubs from 2022 to 2023 Cymru Premier.

Draw
The draw was made on 17 August 2023 at 13:00 live on the SPFL YouTube Channel.

Teams that entered the competition in the third round.

Fourth round
The draw was made on 14 September 2023 at 13:00 live on the SPFL YouTube Channel.

No new teams enter in this round.

Teams in Italics were unknown at the time of the draw.

Quarter-finals
The quarter-final and semi-final draws were made on 19 October 2023 at 13:00 live on the SPFL YouTube Channel.

Teams in Italics were unknown at the time of the quarter-final draw.