Both sides begin the 2021-22 season following draws in recent friendlies, as the hosts were pegged back in a 1-1 stalemate with Pollok while Raith Rovers played out a 2-2 draw with Queen's Park.
A club of Cowdenbeath's stature will certainly not be expecting any miracles in the upcoming Scottish League Cup campaign, but two respectable pre-season draws heading into the tournament do serve as cause for optimism for Gary Bollan's side.
Having managed to hold Premiership side Dundee United to a 1-1 draw - during which Kris Renton cancelled out Lawrence Shankland's opener - a trip to non-league Pollok followed for Cowdenbeath, who were on course for a victory thanks to Liam Buchanan's opener before Gary McCann's equaliser saw the spoils shared.
A fired-up Cowdenbeath could hardly have dreamed of a more appropriate start to the League Cup than against their Fife rivals Raith Rovers, although they ended the 2020-21 competition with just one point to their name from four group matches.
Three more taxing fixtures against Brechin City, Alloa Athletic and Livingston also lie in wait for Bollan's men, who will simply hope to give a good account of themselves before their league campaign gets underway later this month.
Meanwhile, Raith's pre-season was a mixed bag to say the least, as the Championship outfit eased past Stranraer and lost to Clyde before welcoming last season's fourth-tier champions Queen's Park to Stark's Park on July 3.
Aidan Connolly drew first blood for Raith before Louis Longridge and Will Baynham turned the game on its head, and it took a 71st-minute equaliser from Livingston loanee Matej Poplatnik to rescue a draw for Raith.
Manager John McGlynn lamented his side's "passive" start to the second half against the third-tier side, and there can be no room for complacency in a fiery Fife derby to kick off proceedings in the Scottish League Cup, where Raith and Cowdenbeath are familiar foes.
Indeed, the two clubs have faced off in the last three League Cup campaigns during the group stage - with Raith winning two compared to a solitary victory for Cowdenbeath - and last season's battle saw McGlynn's side win 1-0 courtesy of a Manny Duku winner.
Veteran forward Liam Buchanan has already made an impression since joining from Alloa Athletic earlier this summer, and the 36-year-old should line up against another one of his former clubs this week alongside Kris Renton.
Raith new boy Poplatnik has staked his claim for a start after netting off the bench during his debut in the draw with Queen's Park, while the hero of last season's cup tie Duku now represents Inverness Caledonian Thistle.
Poplatnik is competing with the likes of fellow new arrival James Keatings and Lewis Vaughan for a start up front, though, and McGlynn is hopeful that Dave McKay can play a part after completing his 16-month recovery from a serious ACL injury.
Cowdenbeath possible starting lineup:
Gill; Mullen, Thomson, Todd, Barr; R. Buchanan, Morrison, Hutton, Swann; L. Buchanan, Renton
Raith Rovers possible starting lineup:
MacDonald; Tumilty, Berra, Benedictus, Dick; Connolly, Tait, Spencer, Zanatta; Keatings, Poplatnik
We say: Cowdenbeath 0-2 Raith Rovers
Both Cowdenbeath and Raith have all the motivation they need to start the season on a high note against their local rivals, and both managers have plenty to ponder following their pre-season results.
In this instance, however, we think the added quality of the new-look visitors' squad will shine through as they open their Scottish League Cup campaign with a comfortable success.
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