The teams of North Zone and Central Zone played against each other in the first match of Duleep Trophy, 1968-69 and the two teams played the match at Delhi from 17-19 January, 1969. The North Zone team batted first in the match and scored a good total of 326 runs in its first innings. The famous batsmen like H Dani, Akash Lal and S Dharsi made most of the contributions to the North Zone total, by scoring their individual half centuries. While replying to the 326 runs of North Zone, the Central Zone batsmen failed to play well in their first innings. As most of the Central Zone batsmen, except L Singh could not play well in the innings, the first innings of Central Zone ended on a small score of only 177 runs. Only L Singh showed some resistance for Central Zone in the innings and became the top scorer for his team with 63 runs. B Bedi and G Inder Dev took 5 and 4 wickets, respectively for North Zone to restrict Central Zone's first innings to such a tiny total. Because of this lead of 149 runs in the first innings, the North Zone batsmen played with more confidence in the second innings and scored 202 runs for 7 wickets. The North Zone captain, H Dani declared the second innings on 202-7 and thus set a target of 352 runs to win for Central Zone. However, the stipulated duration of the match got over by the time the Central Zone team reached the score of 106-5 and as a result, the match ended on a draw. The match officials declared the North Zone team as the winner of the match on the basis of its lead in the first innings. The North Zone team was also allowed to play in the Semi-Finals of Duleep Trophy, 1968-69.
The first Semi-Final of Duleep Trophy, 1968-69 was played between the teams of East Zone and South Zone and the match was held at Calcutta from 17-19 January, 1969. The match saw the South Zone team batting first in it and scoring a small total of only 188 runs, due to some poor batting display from the batsmen. None of the South Zone batsmen, except the captain, M Jaisimha could play well in the first innings. Jaisimha scored 69 runs in the innings to become the top scorer and also to help his team in getting the total. Though the bowlers bowled quite well and also well restricted South Zone innings to such a small total, yet the East Zone batsmen failed to capitalise on the bowlers' good performance. They miserably failed to read the spin of E Prasanna and S Venkataraghavan and got all out for a mere total of only 153 runs in the first innings. Both Prasanna and Venkataraghavan took 4 wickets, each for South Zone in East Zone's first innings and helped their team take a lead in the first innings. However, the poor performance of the South Zone batsmen continued in the second innings also and they could score only 140 runs in the innings, before getting all out. Chasing a target of 176 runs to win, the East Zone batsmen failed to show a good batting display and got all out to only 48 runs in their second innings. S Venkataraghavan and Abid Ali caused most of the damages to the East Zone batting line-up and they took 4 and 3 wickets, respectively for the South Zone. The South Zone team won the match with a margin of 127 runs and entered into the Final of Duleep Trophy, 1968-69.
The West Zone and North Zone teams appeared against each other in the second Semi-Final of Duleep Trophy, 1968-69 and the match took place at Bombay from 08-10 February, 1969. Winning the toss, the captain of North Zone, H Dani took the decision of fielding first in the match. Being put into bat first, the West Zone team showed a wonderful batting performance in the first innings and scored a huge total of 443 runs by losing 9 wickets, before declaring the innings. The famous all-rounder, Eknath Solkar scored a brilliant century of 145 runs and A Mankad played an innings of 77 runs to help West Zone get the huge total. The North Zone batsmen faced lot of troubles in their first innings, while replying to the 443 runs, made by West Zone in the first innings. None of the North Zone batsmen could play well and as a result, North Zone got all out to a mere score of only 187 runs in the first innings. The North Zone team had to follow on in the second innings, as it was trailing by 260 runs in the first innings. However, the match ended on a draw after only 1 over was bowled in North Zone's second innings and the match officials declared West Zone as the winner for having a lead in the first innings. The West Zone team also reached the Final of Duleep Trophy, 1968-69 to play against South Zone.
It was once again a battle between the teams of South Zone and West Zone in the Final of Duleep Trophy, 1968-69. The two teams had played against each other in the Final of the tournament for several times before the eighth edition and South Zone became the winner in the previous two consecutive editions. This time, South Zone and West Zone played against each other in the Final of Duleep Trophy, 1968-69 at Hyderabad from 28 February-03 March, 1969. The toss of the match was won by the West Zone skipper, C Borde and he decided to bat first in the match. His decision was proved to be a right one, as the West Zone batsmen played well and scored a good total of 333 runs in the first innings. The opener, C Chauhan played a brilliant knock of 103 runs for West Zone and the other opener, D Sardesai also scored 60 runs. In reply to the 333 runs, made by West Zone in the first innings, the South Zone team failed to show a good performance with the bat. The West Zone bowler, A Pai bowled brilliantly to take 6 wickets for 93 runs and he played an important part in restricting South Zone's first innings to only 251 runs. The West Zone batsmen played better in the second innings and scored a better total of 388-7, before declaring the innings. Two West Zone batsmen like A Wadekar and V Bhosle scored centuries in this innings. Wadekar scored 144 runs and Bhosle scored 126 runs to help their team getting a huge lead of 470 runs over South Zone in the first innings. The South Zone team batted in the second innings with a target of 471 runs to win and it was totally impossible for them to achieve the target, as there was not much time left in the match. The stipulated duration of the match ended when South Zone reached the score of 143-4 in the second innings. The match officials declared the West Zone team as the winner of the match as well as the championship title of Duleep Trophy, 1968-69, for having a lead in the first innings.