Scottish Challenge Cup: Dunfermline face Boreham Wood; Airdrie face Sutton
Boreham Wood host Dunfermline Athletic and Sutton United visit Airdrieonians as English teams play in the Scottish Challenge Cup for the first time.
The two National League teams enter the competition at the second-round stage.
Two Premiership Under-21 teams are guaranteed a place in the third round following Thursday's draw.
Dundee Colts were drawn at home to their Motherwell counterparts, while St Mirren's Under-21s are up against Hamilton Academical's youngsters.
Accies were the only colts team out of 12 to beat a senior side in this week's first-round ties, thumping League Two leaders Clyde 4-1, with three progressing after overcoming other under-21 outfits.
Clubs from Northern Ireland, Republic of Ireland and Wales have played in the competition previously and also enter at the second-round stage, with matches to be played on 8 or 9 September.
Former Rangers midfielder Stuart McCall helped with the draw and thought the introduction of English sides added some additional excitement.
"It's something different, something fresh," he told BBC Scotland. "I know they were desperate to get involved in it, the two sides, so it will be something to look forward to."
Welsh champions The New Saints, who face Midtjylland in Europa League qualifying on Thursday, were handed a home tie against League Two outfit Queen's Park.
Connah's Quay Nomads, who finished third in the Welsh Premier League, are away to Falkirk.
Northern Ireland champions Crusaders also face Scottish Championship opposition, away to Queen of the South, while runners-up Coleraine host Highland League side Formartine United.
League of Ireland outfit Sligo Rovers, who replaced Bray Wanderers following their financial problems, are at home to either Forfar Athletic or Livingston Colts, their tie abandoned on Tuesday because of a power failure.
Peterhead host the other Irish side, Bohemians, while another League Two side, Edinburgh City, visit Lowland League champions East Kilbride.
Dunfermline knocked out holders Inverness Caledonian Thistle 2-1 on Tuesday and their reward is a trip to Borehamwood in Hertfordshire to face the side who missed out on promotion to England's League Two after losing in the play-off final to Tranmere Rovers.
Sutton, who finished one place above Boreham in the league but lost to them in the play-off semi-final, travel to face League One Airdrieonians.
Scottish Challenge Cup, second round draw
Airdrieonians v Sutton United
Arbroath v Annan Athletic
Boreham Wood v Dunfermline Athletic
Coleraine v Formartine United
Dumbarton v Montrose
Dundee Colts v Motherwell Colts
Dundee United v Alloa Athletic
East Fife v Partick Thistle
East Kilbride v Edinburgh City
Falkirk v Connah's Quay Nomads
Peterhead v Bohemians
Queen of the South v Crusaders
Ross County v Raith Rovers
Sligo Rovers v Forfar Athletic or Livingston Colts
St Mirren Colts v Hamilton Academical Colts
The New Saints v Queen's Park
Ties to be played 8/9 September