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Gaikwad (99 off 57 balls) and Conway (85 not out off 55) put SRH’s attack to the sword, notching up a scintillating 182-run partnership, the highest opening stand of the season, as CSK posted an imposing 202 for two after being invited to bat.
In reply, SRH fell short, reaching 189 for 6 in 20 overs despite late heroics from Nicholas Pooran (64 not out) and a 47-run innings by skipper Kane Williamson at the top.
Choudhary emerged with the best figures for CSK, scalping four for 46, while Mitchell Santner (1/36) and Dwaine Pretorius (1/40) took one wicket each.
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Abhishek Sharma (39) and Williamson gave SRH a flying start to their chase but Choudhary struck twice in two balls to reduce the Hyderabad outfit to 58 for 2 in six overs.
While Sharma was caught by Dwaine Pretorius at long-on, Rahul Tripathi was out for a duck after giving catching practice at short third man.
Aiden Markram hit two sixes before falling prey to Mitchell Santner.
Pooran hit Ravindra Jadeja for a six before unleashing a monstrous reverse sweep for another maximum, while Williamson too notched up a one-handed six to keep the scoreboard ticking.
The SRH skipper, however, was trapped in front by Pretorius as it became 126 for 4 in 15th over.
Pooran then kept fighting in vain while scoreboard pressure took a toll on the other batters.
Earlier, Gaikwad, who has been blowing hot and cold this season, was at his destructive best as he smashed six sixes and as many fours before tragically falling short of a ton by just one run.
The 25-year-old was in his zone as he stood on his backfoot, and played some exceptional shots to dominate the formidable SRH bowling unit.
Anything short was pulled with immaculate ease, while pitched up deliveries were treated with equal disdain as Gaikwad didn’t miss a trick to send SRH on a leather hunt during his classy innings.
Conway too showed great temperament as he was the perfect foil for Gaikwad. He bide his time initially before going for the big shots in the slog overs.
Bhuvneshwar Kumar (0/22) was the best bowler on display for SRH, while pace sensation Umran Malik had a really bad day in office, having conceded 48 in his four overs. T Natarajan (2/42) picked up two wickets but also went for runs.
With Washington Sundar suffering an injury while fielding, SRH was forced to use Markram and Shashank Singh as the fifth bowler, who conceded 46 from their combined four overs.
After a watchful start, Gaikwad broke free as he pulled Marco Jansen for two maximums, while Natarajan was sent across the mid-wicket boundary as CSK reached 40 for 0 after the powerplay.
Gaikwad was particular harsh on Malik, smashing him over cover first before lifting him over long-on for another maximum in his first over.
Malik cranked up the pace, bowling the fastest delivery of the tournament, clocking 154kmph in the 10th over, but ended up conceding two more boundaries off Gaikwad’s blade as the opener completed his half-century off 33 balls.
Markram too faced the fury of the duo with Conway sending him across the fine leg before going down the wicket for a flat six.
Gaikwad too clobbered him for successive sixes as the 100 was up in the 11th over.
Malik was again in the line of fire as Gaikwad slogged him over long-on for a boundary before lifting him over long-off for another maximum.
A top-edge six off Marco Jansen, meanwhile, helped Conway bring up his fifty in 39 balls and he ended the 15th over with another four and a six.
Natarajan was brought back but he too conceded 13 runs with Gaikwad producing another pull. Conway too sent one over the bowler’s head in the 18th over.
Gaikwad, however, missed out of a deserving hundred when he gave an easy catch at point.
Back at the helm of affairs, M S Dhoni promoted himself but couldn’t make an impact as he was holed out by Malik off Natarajan.