It’s a break from the league action now with the Premier Sports Cup last 16 ties taking place this week. With ten sides from the Premiership, five from the Championship and one from league one, who will reach the quarter finals?

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Kilmarnock V Ayr

The Ayrshire derby has been chosen for the Friday night slot and it’s the first time that the two will meet for four years. Kilmarnock won the last clash 3-1 en route to their championship title. Four years down the line, who will come out on top? A few weeks ago, at the dawn of a new season with optimism brimming, Neil McCann publicly stated ambitions to reach a cup final. With the Premier Sports Cup knockout rounds commencing, they have the opportunity to get one step closer to doing just that. Moreover, being drawn against a Championship side in Ayr is a favourable draw for Killie. Yet, even allowing for that, with nine goals conceded in the opening two matches, McCann’s main focus should be making his side competent facing their own goal again. Their opponents, Ayr, will be quietly confident They have excelled so far away from home, beating Falkirk in the group stages and earning a point away to Dunfermline at the weekend. In contrast, they have conceded just two goals in their last five matches, scoring 11 in the process. So, with the visitors so solid at the back and the home side likely looking to return to basics, this battle may not be the most attackingly pleasing for the neutral.

The Prediction: Kilmarnock 0-0 Ayr (Ayr to win on penalties)

Aberdeen v Dundee

Aberdeen will be looking for instant revenge after a disappointing 2-0 loss at Dens Park last week. The Reds have had a mixed start to the season, with the highs of a 3-2 victory against Hearts followed by a dismal display in the city of discovery. In reality, it could have so easily been two losses from two and a whole lot of questions being asked about Stephen Robinson’s side. Make no mistake, the Northern Irishman has been brought in to propel Aberdeen back up to the top end of Scottish football; and on the basis of the opening two performances, there is still a lot of work to do. It’s still early days though and a win in the Premier Sports Cup would ease some nerves. Their opponents, Dundee, will be very happy with their start to the campaign. A 1-0 loss at Celtic Park is hardly shameful, while their display last week could be a positive sign of things to come throughout the season. Steven Pressley last week admitted pride while stating it was the “most complete performance” of his tenure. With Aberdeen at home, the dynamic changes; however, I still expect it to be a really tough afternoon for the 2025 Scottish Cup Champions, being pushed all the way to penalties.

The Prediction: Aberdeen 1-1 Dundee (Aberdeen to win on penalties)

Dunfermline v Ross County

This is one of those games you would regard as a good draw for both sides. Dunfermline, who made the Scottish Cup final last season, have continued in a similar vein this season, securing a place in the knockout rounds with an impressive away victory against St Mirren. Defensive solidity has been key, with just two goals conceded in their last five; however, they have struggled up top, scoring just one in the opening two league matches. With two draws from their opening two Championship matches, question marks remain over whether they can make that final step of promotion. Their opponents, Ross County, are battling it out in the third tier of Scottish football for the first time in nineteen seasons. As expected, they have won their opening two league matches and are heavy favourites to be promoted. So how will this battle fare? Despite an underwhelming start to the league, Neil Lennon’s Dunfermline have confidence in the knockout stage, with the successes of last season to call upon. They will prove too much for the Highland visitors.

The Prediction: Dunfermline 3-1 Ross County

Dundee United v Celtic

After a 4-0 loss to Hearts, welcoming Celtic to Tannadice is quite a daunting prospect for Dundee United. In last week’s trip to the capital, they were defensively exposed and lacked any real bite going forward. Against a Celtic side that just put five past Kilmarnock (and it could have been more), all the signs seem to be pointing to a comfortable away victory. Yet, football doesn’t always work like that; the Tangerines showed they can be a problem for the Champions last season, winning both matches at home. However, it’s early days, but this Celtic team does look a much stronger outfit. With over £20 million spent on Kasper Høgh, Camilo Duran and Haissem Hassan in attack, the Hoops are finally making moves in the transfer window. Rumours around Mika Baur and Gvidas Gineitis also swirl on the transfer front. With Martin O’Neill back in the dugout after a minor operation, expect Celtic to continue their convincing start to the season.

The Prediction: Dundee United 0-3 Celtic

Hearts v Inverness

Later tonight, Hearts will face Benfica, one week after a 6-1 hammering. You can only hope for their sake that the Portuguese giants take their foot off the gas and play a reserve team; otherwise, another ugly result will likely occur. Nevertheless, on the domestic front, Hearts got back to winning ways with a 4-0 victory against Dundee United last week. It was exactly what the doctor ordered after an underwhelming start to Wouter Vrancken’s reign. The Belgian suffered some criticism for the European displays but will have been relieved to get his first win on the board. Inverness are unbeaten so far this season and haven’t conceded a goal in their last five matches. So, they will be coming to the capital well drilled and looking to cause an upset. However, the Jambos’ domestic performances have been impressive, exerting an in-possession control that wasn’t even present for large periods of last season, so I expect them to overcome this in routine fashion.

The Prediction: Hearts 2-0 Inverness

Hibs v Partick Thistle

It’s a massive night tonight for Hibernian as they take on Shkendija in the second leg of their Conference League qualifier. A late winner midweek against the North Macedonians could prove crucial in setting up a likely play-off clash with K.A.A Gent. Morale will be high as well after a heroic 2-1 victory at Ibrox at the weekend. Partick Thistle will be gutted to have missed out on Scottish Premiership status last season with yet another play-off defeat, this time at the hands of St Mirren. Now favourites for the Championship title, they have started the season strongly with two wins from two. So, can they make it three from three? It’s a tall ask, it genuinely is, but I wouldn’t write them off. The Hibees will no doubt exert themselves physically tonight in Europe and return to Scottish football a jaded outfit. So, it’ll be interesting to see whether the Jags can take advantage of this and claim their first major cup scalp under Mark Wilson’s guidance. I think they might just do that and cause a major upset.

The Prediction: Hibernian 1-2 Partick Thistle

Stenhousemuir v Motherwell

The rise of Stenhousemuir has been a terrific story in the World of Scottish Football. A League Two side just three seasons ago, they return to the second tier of league football for the first time in 28 years. Moreover, they seem just at home, with four points from the opening two games suggesting they will be a competitive outfit throughout the season. However, their opponents Motherwell will prove a different level of quality than what they have faced so far. Alfred Johansson’s side will look to progress to the Conference League play-off against Helsinki tonight and if he manages to do so, it would be an incredible achievement for the Swede and calm fears that life after Jens Berthel Askou will be doom and gloom. No matter the result tonight, though, you would expect the Steelmen to face few problems on Sunday.

The Prediction: Stenhousemuir 0-3 Motherwell

Rangers v St Mirren

Already, you feel that this game will be crucial for Derek McInnes’ future as Rangers boss. It should be too early for sacking rumours to surface; however, should Rangers exit the Premier Sports Cup in a home match against St Mirren, such talk will only intensify. The Gers face Jagiellonia Bialystok tonight and if last week’s match is anything to go by, they will have to work extremely hard to overturn that deficit. The Polish side have dangerous players in attack but did suffer an unexpected home defeat to Widzew Lodz at the weekend. St Mirren travel to Glasgow looking to build on their positive start to the season. With two wins from two, they have calmed relegation fears and reminded us that they can be a competitive outfit in the top tier. Nevertheless, I believe that this will be the day that Rangers get their first domestic victory of the season. Even if it’s less than pretty.

The Prediction: Rangers 1-0 St Mirren