The sides have not met since being involved in a tight race for the League One title in 2019-20 when the coronavirus struck with Raith one point ahead, the teams still to play and Falkirk boasting a vastly superior goal difference, but the league was called in the Kirkcaldy club’s favour to the Bairns’ chagrin.
The tie – also a repeat of the 1913 final – is one of the stand-outs of the draw which also includes Partick Thistle and Dunfermline who met in a mirror image, and goal-less, cinch Championship fixture at the weekend.
Dundee United defender Charlie Mulgrew also paired Championship leaders Inverness Caledonian Thistle with fellow second-tier side Morton and teed up an Angus derby between Arbroath and Forfar Athletic.
The cinch League One leader Queen’s Park will host the highest ranked side to enter the draw at this stage, last season’s 11th placed Premiership side Kilmarnock, in a repeat of an SPFL Trust Trophy match earlier this season. Stenhousemuir and Airdrie will also reprise their earlier Premier Sports Cup encounter in the national competition’s third round next month.
Hamilton who, like Kilmarnock, dropped out of the top flight last season face a banana skin in Ayrshire at Auchinleck Talbot’s Beechwood Park and Brora Rangers face the long trip to Ayr United, if they can overcome Albion Rovers in their replay next week.
An all-Edinburgh derby is in prospect – if Lothian Thistle Hutchison Vale can see off Dunbar in the sides’ replay following their 1-1 draw at New Countess Park. The duo were drawn at home to Gary Naysmith’s Edinburgh City who defeated Bo’ness United to qualify. Competition debutants Sauchie Juniors have been drawn with League One Dumbarton, while Darvel’s maiden entry to the tournament has sent them to Brechin City after their win at Stranraer on Saturday.
In total, four ties are yet to be decided with three awaiting replays and Clydebank hosting Elgin City in the remainibg second round tie on Monday evening, live on BBC Scotland. The winner is at home to Clyde.
Ties will be played on the weekend of November 27.