In the Duleep Trophy, 1998-99, all the five regular participating zonal teams played against each other with the same objective of winning the championship title. The teams were selected by the Board of Control for Cricket in India (BCCI) from five different geographical locations of India. Being named as the Central Zone, East Zone, West Zone, North Zone and South Zone, the teams actually represented their respective zones in the tournament. The Duleep Trophy has already become one of the top class and most popular domestic cricket tournaments in India. It has also presented a large number of talented cricketers to the Indian national cricket team. As all the teams vied for the championship title, the Duleep Trophy, 1998-99 eventually became a highly competitive tournament, which the cricket enthusiasts of India liked very much.

The match between the teams of North Zone and South Zone was the first match of Duleep Trophy, 1998-99 and the match was held at Mumbai from 01-05 December, 1998. After the South Zone captain, S Raju won the toss; he invited the North Zone team to bat first in the match. The decision was proved to be a good one, as the South Zone bowlers did well to restrict North Zone`s first innings to 225 runs, while bowling first in the match. Only R Nayyar played well for North Zone in the first innings, as he scored 52 runs for his team. While replying to the first innings total of North Zone, the South Zone batsmen faced some troubles; however, they eventually batted well to surpass North Zone`s first innings total. South Zone declared its first innings on a score of 254-9, after taking a lead of 29 runs over North Zone in the first innings. Playing with a deficit of 29 runs in the first innings, the North Zone batsmen played wonderfully and scored a huge total of 445 runs for 9 wickets in their second innings. The opener and skipper, V Rathour played the anchor role in North Zone`s second innings by playing a wonderful knock of 136 runs. P Dharmani (72) and V Sehwag (70) also made their own contributions to North Zone`s second innings. H Ramkishen bowled nicely for South Zone and took 6 wickets for 141 runs in North Zone`s second innings. The South Zone batsmen required 417 runs in the second innings to win the match; however, they failed to play well and got all out for only 189 runs. Thus, the North Zone team won the match with a huge margin of 227 runs and also entered into the Semi-Finals of Duleep Trophy, 1998-99.

The teams of Central Zone and North Zone played against each other in the first Semi-Final of Duleep Trophy, 1998-99 and the match took place at Valsad from 09-13 December, 1998. The Central Zone skipper, G Khoda took the decision of fielding first in the match, after winning the toss and it was proved to be just the perfect decision. The Central Zone bowlers bowled extremely well and restricted North Zone`s first innings to a tiny score of only 113 runs. None of the North Zone batsmen could stand before the disciplined and brilliant bowling of S Bangar and M Kamal, who took 5 and 4 wickets, respectively for Central Zone. The Central Zone batsmen showed a wonderful batting display while replying to the small first innings total of North Zone. The Central Zone batsmen scored a good total of 346 runs 9 wickets, before their captain declared the innings. The opener, JP Yadav (84), S Bangar (67) and Y Ghare (66) scored most of the runs for helping Central Zone in taking a lead of 233 runs over North Zone in the first innings. Though the team was trailing by a huge margin of 233 runs in the first innings, the North Zone batsmen played extraordinarily in their second innings and scored a huge total of 467 runs, before getting all out. V Dahiya (92), R Nayyar (91) and V Sehwag made most of the contributions in North Zone`s second innings. Thus, the Central Zone batsmen required 235 runs in the second innings to win the match and they eventually scored 238 runs by losing 5 wickets. The skipper, G Khoda led his team from the front by scoring 81 runs and he got good accompany from M Kaif, who scored 51 runs for Central Zone. The Central Zone team reached the Final of Duleep Trophy, 1998-99 by winning the match with a margin of 5 wickets.

West Zone and East Zone were the teams that played against each other in the second Semi-Final of Duleep Trophy, 1998-99 and the match was held at Rajkot from 09-13 December, 1998. Winning the toss, the captain of West Zone, S Bahutule took the decision of batting first in the match. The West Zone batsmen gave a wonderful response to their captain`s decision, as they scored a huge total of 473 runs in their first innings. S Kotak became the top scorer for West Zone by scoring a wonderful century of 109 runs and P Mhambrey also played well to score 81 runs. S Bahutule (70) and A Kale (62) made their own contributions to West Zone`s first innings total, as well. The East Zone batsmen also showed their class and talent while replying to the huge total of West Zone and they scored another huge total of 426 runs in their first innings. The opener, N Haldipur played a magnificent century knock of 170 runs to become the top scorer for East Zone. However, the East Zone team could not surpass the first innings total of West Zone and it had a deficit of 47 runs in the first innings. When, the West Zone team reached the score of 72-2 in the second innings, the stipulated duration of the match got over and the match ended in a draw. The match officials declared the West Zone team as the winner of the match, as it had a lead in the first innings and the team also entered into the Final of Duleep Trophy, 1998-99.

The West Zone and Central Zone teams played against each other in the Final of Duleep Trophy, 1998-99 and the two teams played the match at Aurangabad from 17-21 December, 1998. The toss of the match was won by the captain of Central Zone, G Pandey and he took the decision of batting first in the match. The decision was proved to be a good one, as the Central Zone batsmen played well and scored a good total of 344 runs in their first innings. M Mudgal was the top scorer for Central Zone with 81 runs to his name and M Kaif also played quite well and scored 69 runs for his team. The West Zone batsmen failed to play as good as the Central Zone batsmen in their first innings and they could score only 281 runs, before getting all out. The West Zone captain, H Kanitkar made most of the contributions to his team`s total by scoring 98 runs. M Kartik bowled brilliantly to pick up 5 wickets for 73 runs on behalf of Central Zone in West Zone`s first innings. After attaining a good lead of 63 runs in the first innings, the Central Zone batsmen scored 203 runs in their second innings, before getting all out. The opener, G Khoda played wonderfully and scored a century of 103 runs for helping Central Zone set a target of 267 runs to win for West Zone. However, the West Zone batsmen failed to achieve the target of 267 runs and they could score only 144 runs in their second innings, before losing all the wickets. A Zaidi took 4 wickets for 44 runs and K Parida picked up 3 wickets for 43 runs to help Central Zone clinching a huge victory of 122 runs in the match. The Central Zone team also clinched the championship title in Duleep Trophy, 1998-99 by beating the West Zone team in the Final.