In April 2014, United announced that they had agreed a deal with German sportswear company Adidas to produce the team kit for the 2014–15 season and beyond, ending the club's previous association with Macron.

[4] On 17 October, Sheffield United announced a two-year deal with local business Blue Portal Telecoms with their logo appearing on the shorts of the first team.

[22] On 29 July, incumbent Player of the Year, Harry Maguire, was sold to Premier League side Hull City for £2.5 million after months of speculation about his future at Bramall Lane.

[24] Two days later United beat Turkish Süper Lig champions Fenerbahçe 2–1 in a charity friendly in aid of the Soma mine disaster,[25] before completing their pre-season fixture list with a 2–0 loss to York City at Bootham Crescent on 2 August 2014.

[28] Later that week youngster Louis Reed signed a three-year professional contract with the Blades,[29] before United's first win of the season came in the first round of League Cup against Mansfield Town.

[36] Following the international break Andy Butler re-joined former club Walsall on an initial one-month loan,[37] and academy product George Willis joined Bradford Park Avenue on a short-term deal.

[45] The Blades' next match was in the Football League Trophy, winning 2–1 away at Hartlepool United on 7 October,[46] two days before Diego De Girolamo joined York City on a short-term loan deal.

[48] Seven days later they were 2–0 victors in a televised away fixture against Bradford City as defender Bob Harris scored his first goal in the club's colours and Marc McNulty netted his fifth of the season.

[51] United made it three wins and three clean sheets in three games with a 1–0 victory away at Crewe Alexandra on 25 October as Stefan Scougall scored his first goal of the season.

[55] On 4 November, Diego De Girolamo was recalled early from his loan spell at York City[56] after fellow striker Michael Higdon had pulled his hamstring during training.

[62] On 18 November, United beat Crewe Alexandra 2–0 at Bramall Lane to progress to the second round of the FA Cup thanks to a brace from Ryan Flynn.

[54] The following day United completed the signing of Kieran Wallace from Ilkeston on a deal until the end of the season whilst academy product CJ Hamilton joined Mickleover Sports on a youth loan.

[73] On 13 December, Sheffield United's first ever senior match with Fleetwood Town ended in a 1–1 away draw as youngster Kieran Wallace made his professional début.

[74] On 16 December 2014, Marc McNulty scored the only goal in a 1–0 home victory over Southampton to send United to the semi-finals of the League Cup with youngster Che Adams making his senior début.

[80] January began with a 3–0 away victory over Queens Park Rangers of the Premier League with Jamal Campbell-Ryce scoring a second half brace.

[83] On 10 January, United beat promotion rivals Preston North End 2–1 at Bramall Lane with Marc McNulty scoring his tenth goal of the campaign.

[87] On 21 January, Tottenham Hotspur took a 1–0 lead in the first leg of the League Cup semi-finals at White Hart Lane with Andros Townsend converting a penalty after Jay McEveley accidentally handled the ball in the box.

[70] The same day, United drew 1–1 away at Preston North End in the fourth round of FA Cup, with Diego De Girolamo scoring his first goal for the club, earning a replay at Bramall Lane.

[95] Later that day, United rounded off January with a 2–0 home victory over promotion rivals Swindon Town with Jamie Murphy coming off the bench in the second half and scoring a brace.

[97] On 3 February, United were knocked out of the FA Cup in the fourth round replay as they lost 3–1 at home to Preston North End despite Jamie Murphy opening the scoring.

[109] On 26 February, Jamal Campbell-Ryce joined former club Notts County on loan for the rest of the season with the option of a recall after 28 days.

[110] On 28 February, the month ended with a 1–1 away draw at Crawley Town with Marc McNulty converting a late penalty to earn United a point.

[98][113] On 7 March, United suffered another 2–1 home defeat, this time at the hands of League One newcomers Fleetwood Town in their first ever visit to Bramall Lane.