Sachin Tendulkar's heroic innings at Chennai in 1999 stopped just short of taking India to victory. © Getty Images

There are many memories that sports fans hold on to when they think back to their favourite moments. Some of the more memorable were well illustrated by Dileep Premachandran in his chronicle of sport’s never-ending highlights reel on this website.

Sometimes though, the memories are of events that didn’t happen at all. While nursing a drink alone, discussing the game just gone by with mates, while reminiscing about the good old days, every sports fan has at some point (or several) thought – ‘What if? What if that delivery had been a yorker and not a full toss? What if the ball had kissed the line instead of falling an inch outside? What if the penalty had not hit the crossbar?’

A twitter conversation between Mahesh Sethuraman (@cornerd) and Siddhartha Vaidyanathan (@sidvee) had me thinking of the ‘What if?’ moments in cricket. Restricting myself to moments that I saw and that dealt with events exclusively on the field of play, there were two that stood out.

Sachin Tendulkar at Chepauk, 1999

The stage was perfect is an abused cliché in sport, but at Chennai in 1999, it truly was. The most intense rivalry, a riveting contest and a situation that had come down to one man standing between an epic victory and a crushing defeat.

Sachin Tendulkar battled a bad back and an attack that comprised Wasim Akram, Waqar Younis and Saqlain Mushtaq for just under seven hours. There is little doubt that had he stayed for a dozen or so minutes more, India would have won a match they ended up losing by 12 runs. When Tendulkar fell, India were 254 for 7. Four runs later, they were all out.

If he had stayed, if he had not misread that delivery from Saqlain, if Akram had dropped that catch at mid-off – how different would Tendulkar’s and India’s history be? Alone, against high quality bowling, in a high-pressure fourth-innings chase – this would certainly have been Tendulkar’s finest knock, checking every box that anyone could demand in a great innings. And it would have ensured that the puerile ‘If Tendulkar scores a century, India loses’ arguments would have never done the rounds – well maybe not never. It would have infused huge self-belief into an Indian side that would continue to stumble when the pressure was highest until VVS Laxman seized history by the scruff of its neck and turned it around two years later.

Before this Test, the last time Pakistan had played in India was in Bangalore in March 1987. In the fourth innings of that match, Sunil Gavaskar, playing his final Test innings, made 96 of the finest. He was the eighth batsman dismissed, and India lost by 16 runs. Given that context, it seemed poetic that the man who carried the Indian batting torch from Gavaskar would restore balance to the universe.

It still feels a little unbelievable that it didn’t turn out that way.

Lance Klusener, Edgbaston 1999

(L to R) Lance Klusener, Allan Donald and Hansie Cronje during the World Cup 1999. South Africa suffered a bitter disappointment in the semifinal after a tie. © Getty Images

A few months after that Sachin innings came a moment that didn’t quite break Indian hearts in the same way, but was probably more significant for world cricket, especially considering what followed. And if you were a cricket fan, some heartbreak was inevitable at the end of the South Africa v Australia semifinal of the 1999 World Cup. There has never before, or since, been a match that had such a clear winner and loser after ending in a tie.

The match requires no recap – Lance Klusener had owned the tournament and got South Africa to the brink before an inexplicable meltdown saw him run last man Allan Donald out, Australia progressing to the final by virtue of a higher Super Six finish.

Steve Waugh, the Australian captain, described the aftermath in his autobiography. “We ran around like prison escapees, not knowing who to grab, totally overcome with excitement.”

Had Klusener taken South Africa through to the final as he seemed destined to, there’s a good chance South Africa would have lifted their first World Cup trophy. And the accumulated historical baggage that South African teams carry into every world tournament now would have been non-existent, as would the ‘chokers’ label.

As for Australia, Waugh notes in the same book that he would almost certainly have been stripped of captaincy –  especially given the fact that Australia hadn’t been all that impressive in the lead-up and initial stages of the World Cup. Instead, he eventually ended as the captain with the best Test win percentage and forged a team that rode on that crest of self-belief to trample all before them for almost a decade.

During one of the frequent rain delays at Wimbledon, Goran Ivanisevic – a perennial crowd favourite and himself no doubt the subject of ‘What Ifs’ in tennis – was once asked how he passed time. With trademark wit, Ivanisevic gave an answer that pithily explained the allure of thinking about what might have been.

“A channel was showing a repeat telecast of the 1992 final again, and I watched it. I don’t know why I torture myself like this. [Ivanisevic had lost a five-setter to Andre Agassi 6-7, 6-4, 6-4, 1-6, 6-4] While watching the fourth set, I thought maybe I’ll win, but of course, I lost.”