Talk of bone-chilling matches, and Tottenham Hotspur has had its fair share. These matches weren’t just thrilling for fans to watch; they actually sent shockwaves through the entire world of betting. The Spurs undoubtedly have unique gameplay characterized by nail-biting comeback matches and dramatic upsets. And we will be exploring a few of them today.

1. The Historic Comeback Against Ajax in 2019

It will be impossible not to include this as one of the Spur’s brightest matches. This match was the second leg of the UEFA Champions League semi-final. It took place on May 8, 2019,  at the famous Johan Cruyff Arena.

Already the Spurs were sitting on a 1-0 loss to Ajax in the first leg of the tie and would require a miracle to get to their first-ever Champions League final. Indeed, what happened there was a true football miracle.

At the beginning of the match, the bookmakers strongly favored Ajax, offering odds around 2.00 for a home win. This showed the high pre-match expectation of Ajax’s attacking prowess. 

On the other hand, things didn’t seem very bright for Spurs and even got worse as Ajax went to the break leading 2-0 and so 3-0 on aggregate. As you can expect, a new live betting market appeared and this time the Dutch side started being backed even more aggressively. However, those looking to take advantage of the situation with free bets found themselves in a rapidly shifting landscape as the match progressed.

The second half was simply magnificent. Lucas Moura completed a hat-trick, in added time to make it 2-3 Spurs and the overall score remained 3-3.  With this Tottenham was able to advance to the finals. This monumental comeback opened up serious repercussions on the betting system, especially those who placed pre-match bets on  Ajax’s win.

2. The Leicester City Title Decider in 2016

A lot rested on this match between Tottenham and Leicester City, as the two teams had reached that poignant moment in time where either could have taken the title of the Premier League.

On May 2, 2016, Tottenham hosted Leicester at White Hart Lane, knowing that the only way they were going to remain in the hunt for the English Premier League title was by getting a win. The tension was unprecedentedly high because it was a culmination of the Leicester miracle and therefore the team had a lot to fight for.

Tottenham were strong favorites at the start of the match, best price on them winning the match 1.55, but very quickly as this match unfolded the punter money switched. The stadium was highly tense with Spurs fans praying that finally, this was it, the time that finally they were going to clinch the title.

The football that followed was astonishing and Tottenham was left worse for the better, which was a 2-2 draw that day. Leicester then won the title the following week with many bettors bewildered by the turn of events on the pitch. 

3. FA Cup Shocker Against Manchester City 

In the same year Tottenham produced that famous comeback against Ajax, they were back in the news when they met Manchester City in the FA Cup quarter-final on 17 April, 2019.

Before this encounter, City were the champions of the premier league and consequently, the odds makers placed them at about 1.60. The home side was seen as the slight outsiders and even many of those placing a wager believed that the away side would triumph to win the match.

This match which was played at the Etihad Stadium was full of incidents as the match proceeded through the variables some of which included VAR controversies to net-breaking goals. Tactically, it was Son Heung-min’s pace and his clinical finishing that put Spurs ahead. Although City equalized after that, Fernando Llorente’s “late winner” sent shivers throughout the bettor’s community.

The pre-match predictions and expectations were starkly different from the game’s outcome. Bettors who risked for Tottenham won while those who staked on City’s dominance left the field questioning their choices.

4. The Champions League Final against Liverpool (2019)

On the 1st of June, 2019 Tottenham progressed to the final of the 2018/2019 Champions League against Liverpool. If you asked any Tottenham fan then, this was a significant milestone for the team. The tension was high, and what was at stake could not be higher. Many bettors were cautiously optimistic, though most bookmakers placed Liverpool as the favorites, with odds at around 2.4 compared to Tottenham’s 3.0. 

Few fans of football would forget the contentious penalty given to Liverpool right from the start which changed the face of the match. Spurs were left disorganized as they struggled to grab the match by the scruff of the neck but were unable to do so and they lost 2-0. 

For those fans and punters who were eagerly waiting for this match, this one was very disappointing;  as it was believed that this specific game would be much more closely contested.

5 Tottenham vs. Aston Villa, 2024

This match was a dramatic 4-1 win that showed the attacking power of Spurs. Such an outcome had few takers because it was expected to be a closely contested match with more even betting toward Tottenham’s loss, perhaps taking on other opponents due to its new attacking flair.

ESPN FC pundit Craig Burley praised Tottenham’s second-half display which was a great comeback for the punch in the nose the team initially received from their opponents. The match was defined by several key moments that turned the course of the game.  First off, Aston Villa took the lead through Rogers as Spurs’ defensive errors during a corner allowed their opponent to open the scoring and set the tone for what was a tough opening half for Tottenham.

Fortunately, just after half-time, Johnson leveled the score with a tap-in from a cross by Heung-min Son. It changed the balance back to Spurs and rejuvenated their attacking intent. This was followed by Dominic Solanke’s quick double (75′, 79′). 

First, with a deft chip over the keeper, and then, after a swift counter-attack, Solanke scored from close range. These goals finally turned the course of the game in Tottenham’s favor.

It then ended with James Maddison’s free-kick. This was the icing on the cake as Maddison netted an excellent free-kick deep into stoppage time to wrap up a dominant win and seal Spurs’ attacking display in the second half of the match.