Tottenham wretched cup draw luck continues with Liverpool away day
Ange Postecoglou may have brought the club's trophy drought to an end via the Europa League in 2025, but Tottenham Hotspur are still without a domestic cup since 2008.
Spurs had been lauded as a "cup team" for much of its history, having claimed eight FA Cups and four League Cups to complement their pair of First Division titles.
However, that tag has faded this century. It's been 18 years since our last League Cup success, back when the competition was sponsored by Carling, and 35 years since the FA Cup set up camp in N17.
It didn't help that the overseer of our most exhilarating era of modern times, Mauricio Pochettino, had little time for cup competitions, and once said that winning trophies merely "builds egos". He wanted the Lilywhites fretting about the most lucrative honours, not the puny League and FA Cups.
Hadn't the Argentine picked Son Heung-min at wing-back in the 2017 FA Cup semi-final against Chelsea, and Michel Vorm in goal at the same stage the following year, his Spurs team may well have gotten too big for their boots instead of, you know, developing a blasphemous trophy-winning habit.
The aforementioned defeats under the arch particularly stung, arguably more so than the pair of League Cup final disappointments we've endured since 2015. In truth, we were comfortably second best in both finals, especially the eerie 1–0 defeat to Manchester City in 2021.
Our trophy craving may have been sated by Ange's and his massive cojones, but our domestic cup toil has continued this decade, and I'm blaming the pesky draw-doers.
Tottenham's domestic cup draws since 2023/24
| Season | Competition & Round | Draw | Result |
|---|---|---|---|
| 2023–24 | Carabao Cup Second Round | Fulham (A) | 1–1 (3–5p) |
| 2023–24 | FA Cup Third Round | Burnley (H) | 1–0 |
| 2023–24 | FA Cup Fourth Round | Man City (H) | 0–1 |
| 2024–25 | Carabao Cup Third Round | Coventry (A) | 2–1 |
| 2024–25 | Carabao Cup Fourth Round | Man City (H) | 2–1 |
| 2024–25 | Carabao Cup Fifth Round | Man Utd (H) | 4–3 |
| 2024–25 | Carabao Cup Semi-Final | Liverpool | 1–4 (agg.) |
| 2024–25 | FA Cup Third Round | Tamworth (A) | 3–0 (A.E.T) |
| 2024–25 | FA Cup Fourth Round | Aston Villa (A) | 1–2 |
| 2025–26 | Carabao Cup Third Round | Doncaster (H) | 3–0 |
| 2025–26 | Carabao Cup Fourth Round | Newcastle (A) | 0–2 |
| 2025–26 | FA Cup Third Round | Aston Villa (H) | 1–2 |
| 2026–27 | Carabao Cup Second Round | Charlton (H) | 5–1 |
| 2026–27 | Carabao Cup Third Round | Liverpool | — |
Look, we haven't been particularly good for much of the 2020s, but my word, we've barely been given a chance.
There was further evidence of our draw misfortune after Wednesday's feel-good trouncing of second -tier Charlton Athletic on Wednesday. Roberto De Zerbi's side blew off some steam after Saturday's 3–0 battering at Brentford, with debutant Sávio scoring one-and-a-half times. Supporters departed with wide grins, but were soon rolling their eyes.
Bloody Jamie Redknapp was at it again, pairing two of his former clubs together in the Carabao Cup third round. There were simple routes to the next stage available, from Peterborough to Leyton Orient, but instead, we're heading to Anfield.
In the past four seasons across both domestic cups, we've been drawn against Manchester City (twice), Manchester United, Liverpool (twice), Aston Villa (twice) and Newcastle United. Of our 14 ties since the start of the 2023–24 campaign, eight have come either against a 'Big Six' member or a 'Big Six' wannabe.
Talk about rotten luck.
