The first match of Duleep Trophy, 1986-87 was played between the teams of Central Zone and East Zone and the match was held at Pune from 20-24 October, 1986. The Eats Zone captain, J Arun Lal won the toss and decided to bat first in the match. The East Zone batsmen responded to the captain's decision wonderfully and scored a mammoth total of 528 runs in their first innings. The captain, J Arun Lal led his team from the front by scoring a magnificent double century of 214 runs and he got wonderful support from A Mitra, who scored 120 runs. The Central Zone batsmen were quite under pressure after their bowlers let the East Zone batsmen score such a huge total in the first innings. However, the Central Zone batsmen batted well and scored a good total of 330 runs in their first innings. Yusuf Ali Khan played a good knock of 111 runs for Central Zone, while Randhir Singh took 6 wickets for 95 runs on behalf of East Zone in Central Zone's first innings. The East Zone was leading Central Zone by a huge margin of 198 runs in the first innings and the match's stipulated duration ended when the team reached the score of 226-2. The East Zone team won the drawn match on the basis of its lead in the first innings and it also entered into the Semi-Finals of Duleep Trophy, 1986-87.
The teams of North Zone and South Zone played against each other in the first Semi-Final of Duleep Trophy, 1986-87 and the two teams played the match at Bombay from 25-28 October, 1986. Winning the toss, the North Zone captain, Madan Lal took the decision of batting first in the match. The North Zone batsmen played well and scored a moderate total of 283 runs in their first innings. The skipper, Madan Lal became the top scorer for North Zone with 55 runs to his name. In reply to North Zone's first innings total, the South Zone batsmen played very well in their first innings and scored a huge total of 364 runs. The batsmen like S Viswanath (91), P Prakash (81) and M Azharuddin (73) scored most of the runs for South Zone in the first innings. The North Zone team batted in their second innings with a deficit of 81 runs in the first innings and they played well to score a good total of 353 runs in their second innings. The North Zone opener, V Lamba played a superb century knock of 104 runs for his team and he got good supports from Y Sharma and A Malhotra, who score 58 and 57 runs, respectively. Chasing a target of 273 runs to win, the South Zone batsmen showed a wonderful batting display in their second innings and achieved the target by losing only 5 wickets. Thus, the South Zone team won the match with a good margin of 5 wickets and also entered into the Final of Duleep Trophy, 1986-87.
The match between the teams of West Zone and East Zone was the second Semi-Final of Duleep trophy, 1986-87 and the match took place at Pune from 25-58 October, 1986. The toss of the match was won by the West Zone skipper, R Shastri and he took the decision of fielding first in the match. However, his decision was proved to be a completely wrong one, as the East Zone batsmen played outstandingly and scored a mammoth total of 561 runs in their first innings. The East Zone captain, J Arun Lal once again led his team from the front by scoring a superb double century of 287 runs and K Dubey also played well to score 70 runs for East Zone. However, though the East Zone team secured such a huge total in the first innings, the West Zone batsmen never got demotivated and they got past the first innings total of East Zone, in their first innings. They score 567 runs for 7 wickets in their fist innings, before the stipulated duration of the match got over. The West Zone captain, R Shastri became the top run-getter for his team, as he remained unbeaten on a huge score of 176 runs. He also got wonderful support from the batsmen like S Gavaskar and C Pandit, who scored 92 and 78runs, respectively in West Zone's first innings. However, as the match ended in a draw, the match officials declared the West Zone team as the winner of the match for having a lead in the first innings. The West Zone team also reached the Final of Duleep Trophy, 1986-87 for playing against South Zone.
The Final of Duleep Trophy, 1986-87 involved the teams like West Zone and South Zone and the two teams played the match at Bombay from 31 October-05 November, 1986. The West Zone team batted first in the match, as its captain, R Shastri decided so after winning the toss. The West Zone batsmen carried forward their wonderful batting form of Semi-Final in the Final match also and they scored a huge total of 516 runs in their first innings. The two openers, A Gaekwad and L Rajput laid the foundation for West Zone's huge first innings total by making a huge opening partnership of 256 runs. While Gaekwad scored a magnificent century of 138 runs, Rajput played a knock of 105 runs for West Zone. The West Zone captain, R Shastri also made his own contribution and played a superb innings of 127 runs for helping his team in getting the huge total on the scoreboard. W Raman took 6 wickets for 123 runs on behalf of South Zone in West Zone's first innings. The South Zone batsmen scored one of the highest team totals in the history of Duleep Trophy, while replying to the mammoth total of West Zone in the first innings. The South Zone batsmen showed their real class in their first innings and scored a huge total of 740 runs, thanks to three brilliant centuries by B Arun, K Srikkanth and C Saldanha. While B Arun was the top scorer with a wonderful century of 149 runs, Srikkanth and Saldanha scored 112 runs and 102 runs, respectively in South Zone's first innings. The other brilliant all-rounder, W Raman also got a huge individual score of 95 runs for helping his team in surpassing the huge first innings total of West Zone. The West Zone batsmen were never seemed to be scared or tensed about the brilliant batting display by their opponents and they played according to their merit in their second innings. As the batsmen like S Keshwala, L Rajput and S Kalyani scored their individual centuries; the West Zone team scored a huge total of 472 runs for 3 wickets in the second innings. While Keshwala remained unbeaten on a score of 124 runs, Rajput and Kalyani scored 109 runs and 101 runs for their team. The other opener, C Pandit also played a good innings of 88 runs. However, as the stipulated duration of the match got over when the West Zone team reached the score of 472-3 in the second innings, the match eventually ended in a draw. The South Zone team was declared as the winner of the match, as it had a lead in the first innings and the team also clinched the championship title in Duleep Trophy, 1986-87.