During Derek Adams' first spell in charge of Ross County, he led them to the Scottish Cup final in 2010.
Now, in 2015, he will embark on his first FA Cup tie in charge of Plymouth Argyle against the team left in the competition which is the nearest geographically to his homeland: Carlisle United.
It will be the second time that the Cumbrians have travelled to Home Park this season. The pair met previously in a league fixture in August, which Argyle won 4-1.
The Pilgrims also have a fine history in the competition, having reached the Semi finals of the competition in 1984 and - more recently - the Quarter finals in 2007, which on both occasions they were beaten 1-0 by Watford.
In recent seasons, after failing to win an FA Cup tie between 2008 and 2013, Argyle have reached the third round and second round in the previous two campaigns and will be hoping for further success this time around.
Standing in their way are two players who are no strangers to the South West in the form of Carlisle manager Keith Curle and new loan signing Mark Ellis.
Curle played for Torquay United during the 1983-84 season, and managed the Gulls briefly in 2007. Ellis, who hails from Kingsbridge, also played for Torquay and was a childhood Argyle fan and one-time mascot.
After Saturday, the Pilgrims will be back in cup action on Tuesday when Millwall come to Home Park for a Johnstone's Paint Trophy Southern Area Quarter Final encounter.