Williams, watched by her family in the stands, lost a heavy first set before leveling the match in the second on Central Court, the place of seven of her 23 Grand Slam titles in singles.
She broke up in the third, but Tan showed his resilience by hitting back to take an exciting final set in a devastating tiebreak.
Asked if this was the last Wimbledon match in her embellished career, Williams said it was a question she “could not answer”.
“Who knows where I’ll jump?” she added.
Williams played his first racing match in nearly a year in Eastbourne last week, partnering with Ons Jabeur in the doubles tournament. The pair reached the semifinals, but had to retire after Jabeur suffered a knee injury.
On Tuesday, she made her long-awaited return to singles, a year after retiring in her last match of the first round of Wimbledon.
The momentum shifted between the two players during the three-hour and 10-minute match – first in favor of Tan when she overcame the first set, then to Williams when she headed to the second.
It looked like the 40-year-old Williams would win the deciding set as he served for the win, but the memorable comeback was not.
Tan lost at 5-5 and although he failed to score at 6-5, he made no mistake when he had a second chance in the tiebreak.
Ranked 115th in the world, Tan played in his first match in the Wimbledon main draw and ninth place in all Grand Slam tournaments.
“When I saw the draw, I was really scared,” she said after the match. “This is Serena Williams – she is a legend. I said to myself, “Oh God, how can I play?” And if I can win one or two games, that’s really good for me. “
Under the lights of the central court, Tan conveniently did more than that – triumphing against one of the greatest athletes the sport has ever seen.
“For my first Wimbledon, it’s a wow. Just wow, ”she added, trying to find the words to capture her emotions.
It remains unclear whether this is Williams’ last appearance at Wimbledon. Asked to summarize her legacy at the tournament, she was succinct, albeit understated.
“I think I’m pretty stable on the grass,” she said. “Maybe not today, but pretty solid there.”
Nadal, Svetek forward
In previous matches on Tuesday at the Central Court, there were victories for this year’s champions of the French Open Rafael Nadal and Iga Sviatek.
Nadal, a two-time Wimbledon winner, survived the fear of beating Francisco Cherundolo 6-4 6-3 3-6 6-4 when he began his pursuit of his 23rd Grand Slam title while Swiatek recorded his 36th consecutive victory. by defeating Yana Fet 6-0 6-3.
Nadal, who missed last year’s tournament due to injury, received a warm welcome on the central court, where he was severely tested by the Argentine Cerundolo.
The Spaniard was looking for a routine victory when he was 2-0 and a break in the third set, but the free swing Cerundolo responded with a double break to take the set.
The match seemed to be moving decisively when the world number 41 tried in the fourth, only for Nadal, to keep the best of himself to the last and to support the victory with a double break.
Swiatek, meanwhile, dominated the first set against Fett in their first game since the French Open, but had to overcome a difficult period in the second when Fett was close to securing a double break.
The most placed recovered from the unstable start of the set and played five consecutive games, increasing her winning streak to 36 games.
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