The South Zone and North Zone teams played against each other in the first match of the Duleep Trophy, 1965-66 and the two teams played the match at Bangalore from 23-25 October, 1965. The North Zone captain, H Dani won the toss and decided to field first in the match. However, his decision was proved to be a wrong one, as the South Zone team put on a huge total of 480-9 on the scoreboard in their first innings. The batsmen like M Jaisimha and A Baig were the stars for South Zone, as they scored 160 and 159 runs, respectively in the first innings. The North Zone batsmen were finding it quite difficult to bat well in their first innings, after the South Zone team scored the huge total. All the batsmen like Akash Lal, H Dani, V Mehra and D Singh scored individual half centuries and helped the North Zone team get a score of 272 runs in its first innings. Having a huge lead of 208 runs in the first innings, the South Zone team declared their second innings on a score of 185-7, thus setting a target of 394 runs to win for North Zone. However, the North Zone team could not achieve the target before the end of play. The team scored 103 runs for 5 wickets in their second innings and the match remained drawn during the specified period of time. The match officials declared the South Zone team as the winner of the match, as it had a lead in the first innings. The South Zone team also entered into the Semi-Finals of Duleep Trophy, 1965-66.
The South Zone team appeared against the West Zone team in the first Semi-Final of Duleep Trophy, 1965-66 and the match was held at Hyderabad from 30 October-01 November, 1965. The captain of West Zone, C Borde decided to bat first in the match after winning the toss and his decision was not proved to be a right one. The West Zone batsmen could not play well in the first innings and got all out to a small score of only 214 runs. After being successful to restrict the West Zone's first innings score to such a mere total, the South Zone batsmen played with confidence in their first innings. The two South Zone batsmen like Nawab of Pataudi and A Milkha Singh got individual centuries and scored 132 and 108 runs, respectively in the innings. As the other batsmen like A Baig and W Khan also played well, the South Zone team eventually scored a huge total of 487 runs in its first innings. Playing with a huge deficit of 273 runs in the second innings, the West Zone team played a bit better and scored 238 runs for 7 wickets. A Wadekar became the top scorer for West Zone in the second innings with a score of 76 runs. However, as the specified period of the match was already over by then, the match officials declared the South Zone team as the winner of the drawn match for having a lead in the first innings. The South team also reached the Final of Duleep Trophy, 1965-66 by winning this match.
The teams of East Zone and Central Zone played against each other in the second Semi-Final of Duleep Trophy, 1965-66 and the two teams played the match at Calcutta from 27-29 November, 1965. The match saw the East Zone captain, P Roy winning the toss and deciding to bat first in the match. The East Zone batsmen played well in the first innings and got a good score of 392 runs, before getting all out. The batsmen like A Roy, P Roy and D Mukherjee made most of the contributions to the first innings total of East Zone. In reply to the first innings total of 392 runs made by East Zone, the Central Zone batsmen played brilliantly in their first innings. With the help of a magnificent innings of 168runs by H Singh, the Central Zone team eventually got a huge score of 416-4 in their first innings. The Central Zone captain, V Manjrekar declared the innings after taking a lead of 24 runs over East Zone in the first innings. However, as the stipulated duration of the match was already over by the time Central Zone finished its first innings, the match ended on a draw. The match officials declared the Central Zone as the winner of the match, as it was having a lead in the first innings. The win also helped the Central Zone team to set up a clash with the South Zone team in the Final of Duleep Trophy, 1965-66.
The Final of Duleep Trophy, 1965-66 was played between the teams of South Zone and Central Zone and the match took place at Madras from 25-27 December, 1965. Winning the toss, the skipper of Central Zone, V Manjrekar took the decision of batting first in the match, though his decision was not well supported by his batsmen. All the Central Zone batsmen failed to play well in the first innings and as a result, Central Zone's first innings ended on a tiny score of only 123 runs. E Prasanna and B Chandrasekhar did most of the damages to the Central Zone batting line-up, as they took 6 and 4 wickets, respectively in the innings. After successfully restricting Central Zone for such a small score of 123 runs, the South Zone batsmen played with a lot of confidence in their first innings. The famous batsman B Kunderan scored century of 100 runs in the innings. As Abid Ali and P Belliappa also played well, the South Zone team eventually scored a good total of 310 runs in the first innings. The Central Zone team batted in the second innings with a huge deficit of 187 runs and as the batsmen failed once again, Central Zone got all out for only 167 runs in the second innings. Thus, the South Zone team won the match with a margin of an innings and 20 runs, while clinching the championship title.