The club finished fourth in the Premier League, qualifying for next season's Champions League, and were eliminated by Crystal Palace in the fourth round of the FA Cup. Additionally, they reached the semi-finals of the EFL Cup where they faced Chelsea. After two legs the aggregate score was 2–2 and Spurs were eliminated 4–2 on penalties. However, after overcoming Ajax on away goals after two very dramatic legs in the semi-finals, Tottenham reached the Champions League final for the first time in the club's history. In an all-English affair, Tottenham lost 0–2 to Liverpool at the Wanda Metropolitano in Madrid.
Notably, the club made no signings during both the summer and January transfer windows. This was the first time in Premier League history where this has been done.[1][2]
For the majority of the season, the club's matches were played at Wembley Stadium due to the development of the Tottenham Hotspur Stadium. On 3 April 2019, the new stadium opened, with the first match being a Premier League game against Crystal Palace. Tottenham won 2–0, with Son Heung-min scoring the first goal at their new ground.
^On 5 January 2019, it was announced that Ogilvie would stay at Gillingham until the end of the season. His loan was initially to end on 31 December 2018.[22]
Overall transfer activity
Expenditure
Summer: £0
Winter: £0
Total: £0
Income
Summer: £2,000,000
Winter: £11,000,000
Total: £13,000,000
Net totals
Summer: £2,000,000
Winter: £11,000,000
Total: £13,000,000
Friendlies
Pre-season
Tottenham took part in the 2018 International Champions Cup with scheduled games against A.C. Milan, Barcelona and Roma.[30] After the three games played by all teams taking part Tottenham was declared champions having accumulated seven points and the best goal difference.[31]
Source: Premier League Rules for classification: 1) Points; 2) Goal difference; 3) Goals scored; 4) Play-offs (only if needed to decide champion, teams for relegation or teams for UEFA competitions). Notes:
^Since the winners of the EFL Cup and the FA Cup, Manchester City, qualified for the Champions League, the spot given to the FA Cup winners (Europa League group stage) was passed to the sixth-placed team and the spot given to the League Cup winners (Europa League second qualifying round) was passed to the seventh-placed team.
Updated to match(es) played on 12 May 2019. Source: Premier League A = Away; H = Home; W = Win; D = Draw; L = Loss
Fixtures
On 14 June 2018, the Premier League fixtures for the forthcoming season were announced.[33] Owing to delays in the completion of the club's new stadium, the first fourteen home games of the season were played at Wembley.[34] Some fixtures were updated after Sky Sports announced their live TV coverage.[35]
Tottenham entered the competition in the third round and were handed an away tie at either Tranmere Rovers or Southport.[36] Tranmere Rovers won the replay 2–0, claiming the home draw to play Spurs.[37]
Due to Wembley Stadium not being available, and Tottenham's new stadium not being complete, the third-round tie against Watford took place at Stadium MK, the home of Milton Keynes Dons.[38]