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The Super Kings won their first game against Kings XI Punjab by 33 runs, after scoring 240/5 which was the highest total of the tournament, a record surpassed by themselves in 2010 by scoring 246 runs. Chennai also managed to win a close match against Mumbai Indians by 6 runs despite Mumbai batsman Abhishek Nayar scoring an unbeaten 45. Then they went on to beat Kolkata Knight Riders comfortably by 9 wickets and Royal Challengers Bangalore by 13 runs in their next two games. But their winning run in the tournament took a hit when their overseas stars Matthew Hayden, Michael Hussey and Jacob Oram had to leave for national duties. Their departure immediately affected their performance as they lost their next three games. The batting, although inconsistent, eventually adjusted to the losses of Hayden and Hussey with contributions from Mahendra Singh Dhoni, Suresh Raina and Albie Morkel. In the home game against Delhi Daredevils, CSK were unable to defend a target of 170 due to half-centuries by Delhi openers Virender Sehwag and Gautam Gambhir. At Jaipur against the home team Rajasthan Royals, the Super Kings batsmen struggled against Pakistani fast-bowler Sohail Tanvir who picked up the best bowling figures in the IPL 2008 (6/14). This was also the best bowling figures in a Twenty20 match until 2011, when Somerset spinner Arul Suppiah took figures of 6 for 5 against Glamorgan. CSK lost another home game to Deccan Chargers which was only the second victory for the latter in the tournament. Chennai beat Delhi Daredevils in their next game by chasing a target of 188, mainly due to the cameos by Vidyut Sivaramakrishnan, Fleming and Morkel. In their next game, Chennai defeated Kings XI Punjab by 18 runs after Subramaniam Badrinath and skipper Dhoni scored half-centuries. The match also witnessed Chennai's Lakshmipathy Balaji claiming the first hat-trick of the tournament and in the process also getting the first five-for (5/24 in 4 overs) in IPL history. However, they were crushed by the Mumbai Indians in Mumbai as opener Sanath Jayasuriya struck an unbeaten 114 off just 48 balls for the home team, to hand a 9-wicket defeat to the Super Kings. In their eleventh match of the season, they beat the Kolkata Knight Riders by 3 runs (D/L method) in a rain-affected match at the Eden Gardens. In the same match, Makhaya Ntini took the third hat-trick of the tournament and won the Man of the match award for his 4/32 in 4 overs. The Super Kings were unable to chase down a modest total of 127 despite being 60/0 at one stage and suffered a shock defeat at the hands of Royal Challengers Bangalore. In another home game, against Rajasthan Royals, CSK went down by 10 runs chasing 212. Albie Morkel's all-round efforts (2/35 in 4 overs and 71 off 40 balls) went in vain as the Super Kings succumbed to a second straight defeat. In their last league fixture, the Super Kings could easily beat the struggling Deccan Chargers by 7 wickets, with Raina scoring an unbeaten half-century. The Super Kings managed to get a semi-final spot with this win as they finished in third place in the league table with 16 points.
The side played their semi-final against the Kings XI Punjab, whom they managed to defeat by 9 wickets, thus entering the final. Electing to bat first, Kings XI scored only 112/8 in their 20 overs as Chennai bowlers dented the innings with wickets at regular intervals. Suresh Raina and Parthiv Patel scored unbeaten fifties and took the team to victory with more than five overs to spare. The Chennai outfit faced the resurgent Rajasthan Royals in the final which was played at the DY Patil Stadium in Navi Mumbai. Batting first, Chennai made a decent total, 163/5, in their 20 overs, with Raina top-scoring with 43 and Parthiv Patel also contributing 38 runs. Rajasthan's run-chase was in trouble at one stage, with the scoreboard reading 42/3 in the seventh over. However, Rajasthan's all-rounder Shane Watson added 57 runs for the fourth wicket with Yusuf Pathan, who went on to score 56 off just 39 balls. With 8 required off the last over for the Royals with 3 wickets in hand, the match went down to the last ball, off which Sohail Tanvir scored a single to give his side the victory. Royals' all-rounder Yusuf Pathan won the Man-of-the-Match award for his all-round performance. The Chennai Super Kings won $600,000 prize money as they finished the tournament as runners-up.
Chennai Super Kings, being the runners-up of the IPL, were among the first sides to secure a berth for the event. However, the tournament was cancelled due to 2008 Mumbai Attacks and Chennai Super Kings, along with Rajasthan Royals, received $1.3 million as compensation.
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