Several professional tennis players were once asked: Over the course of a one-week tournament, which day would you be satisfied at last exiting the tournament? The most frequent answer was Friday – a quarterfinal appearance.

But when Jimmy Connors was asked this, he replied with a trademark counterpunch: “What do you think is the only day that matters for me?”

The implicit answer: Sunday – the finals. No man in the Open era has played more singles finals than Connors. On this Sunday, October 22, 1989, in Tel Aviv, Connors prepared to play his 164th, in hopes of winning his 109th singles title.

It had been an epic career. Connors won his first singles championship as a teenager and continued to rack up victories well into his 30s. The first had come in January 1972. In Jacksonville, Florida, Connors beat veteran American Clark Graebner in the finals. From there, Connors was off to the races, winning five more tournaments in ’72. Many years, the Connors title tally hit double digits – 11 in 1973, 15 in ‘74, 12 in ’76, 10 in ’78.

Fittingly, Connors reached the century mark at his favorite tournament, the US Open, taking the title in 1983 with a satisfying four-set victory over Ivan Lendl. In 1984, the year Connors turned 32, he earned five titles, the fifth coming in Tokyo, where once again Connors beat Lendl in the finals – tournament win number 105.

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Connors' record 109 singles titles still stands to this day.

Connors' record 109 singles titles still stands to this day. 

But then came a surprising drought. Though over the next three years, Connors played consistently enough to remain a top ten mainstay, not once during this time did he win a singles title. Nine times from 1985-’87, Connors reached finals. The drought continued in early ’88, Connors the bridesmaid at tournaments in Milan and Key Biscayne.

Finally, in July, in Washington, D.C., Connors once again lifted the champion’s trophy. Later that year came a triumphant run in Toulouse.

A year later, the 37-year-old Connors defended his title in Toulouse with a sparkling 6-3, 6-3 win over his fiercest rival, John McEnroe. The next week, Connors headed across the Mediterranean to Israel.

His opponent in the finals was Israeli Gilad Bloom, a crisp-hitting, 22-year-old lefthander then ranked 181 in the world who a year later would reach a career-high of 61. Bloom surprised Connors in the first set, taking it 6-2 and breaking serve to start the second. But, as he had so often, Connors rebounded sharply, taking the next two, 6-2, 6-1. As Bloom recalled years later in a New York Tennis Magazine article, “Connors changed his game completely and started attacking my serve relentlessly, even coming to the net on my first serves! This was not his usual game, but it surprised me and changed the match completely. He simply raised his level of play.”

Title 109 proved to be Connors’ last – a record that still stands (Roger Federer is second with 103).

Bloom on this day had joined a large club: Competitors overtaken by a man as tenacious as anyone in tennis history. As Connors liked to say, “I hate to lose more than I love to win.”