T&T outbatted, outbowled and outfielded Mahendra Singh Dhoni's outfit as they chased down a paltry target of 119 in only 15.1 overs to pip CSK to the top position in group by virtue of better net run-rate.
T&T needed to win the match in 17.4 overs but they achieved the feat 2.3 overs in advance to enjoy a far better net run-rate of +0.816 than CSK's +0.271.
T&T will thus meet Mubai Indians in the second semi-final on Saturday while CSK will travel to Jaipur where they will meet Rajasthan Royals, who have remained unbeaten at the Sawai Man Singh Stadium, in the first semi-final on Friday.
For T&T, medium pacer Rayad Emrit (3 for 21) was the most successful bowler while Ravi Rampaul claimed two wickets besides Simmons. Mystery spinner Sunil Narine (12 in 4 overs) kept a tight leash on the CSK but went without a wicket.
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It was a match where CSK performed well below par and much of the blame should be taken by their batsmen who failed to notch up a decent enough total. With seven players failing to reach double digits and poor running between the wickets leading to three run-out was like insult to injury.
While Ravichandran Ashwin (1/24) was economical and Suresh Raina (1/16) did his bit to contain the T&T batsmen, left-arm spinner Ravindra Jadeja was taken to the cleaners by Simmons who scored the bulk of the 30 runs the Saurashtra all-rounder gave away in two overs.