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United’s 2014/15 season started with two major departures. In July, Ryan Gauld joined Sporting Lisbon for a fee of £3 million, whilst in the same month, Andy Robertson would move to Hull City for £2.85 million. United’s recruitment for the season included Charlie Telfer, Blair Spittal, Jaroslaw Fojut, Simon Murray, Henri Anier and Ryan McGowan.
United started their league campaign with an impressive six wins from their first 8 games, losing only to Celtic. Inconsistency would follow United for the remainder of the year, with the Terrors unable to string a run of wins together to move up the league table. United fans' highlight of the season was undoubtedly the New Year's Day thrashing of local rivals Dundee. The 6-2 victory came courtesy of goals from Armstrong, 2 from Mackay-Steven, Erskine, Fojut and Telfer. In the second half of the season, a run of 7 games without a win would prove too much for United to finish any higher than fifth in the league.
In the Scottish Cup, United reached the quarter-final stage. After a 1-1 draw against Celtic at Tannadice, United lost the replay 4-0.
Stuart Armstrong and Gary Mackay-Steven Steven would leave the club in the February of this season for £2 million and £200,000 respectively, both to Celtic.
United’s best success in any competition this season would prove to be the League Cup. A 3rd round win against neighbours Dundee was followed with a thrilling 3-3 encounter with Hibernian after extra-time in the quarter-final. United would win the penalty shoot-out 7-6. Next up came Aberdeen in the semi-final and goals from Morris and Ciftci set up a final against Celtic. Unfortunately, United couldn’t make it 4 wins out of 4 against Premiership opposition as they lost 2-0 at Hampden Park.