Its hard to book an entire year. For example a previous post completely ignores Lex Luger, barely mentions 5 time WWE Champ Brett Hart, and hardly utilizes Flair (In early 99 upon his return only Goldberg was more popular with fans) or DDP (Most watched match on TV in 1998: DDP vs Goldberg).
That said I wont even try to book whole company. 99 featured two huge mistakes by WCW that alienated their audience and wrestling fans in general. Goldberg was the hottest thing not named Steve Austin in all wrestlin, he was bigger than Sting, Rock, Taker, everyone, yet in early 99 he was immemiately pushed into the midcard, just after being World Champ. His re match vs Nash should have main evented SuperBrawl and an all out feud vs Nash should have been the precursor to a re match vs Hogan, a huge potential money maker that never took place. Hogan-Goldberg, after much NWO shenanigans, should have main evented The Great Am Bash.
2nd mistake was immediately booking Flair to look weak and be buried by NWO. Fans had been waiting almost a year to see Flair return and get these guys. Having him job in ridiculous fashion at SuperBrawl to Hogan (Torrie Wilson, hired by Nash, seduces the totally un-charismatic David Flair to turn on his dad and join Hogan?!). Erase that whole thing. If they want to make some money off Flair-Hogan have them face off at SB in a non-title match but with WCW Presidency at Stake and Flair wins. Flair pushes for a title match vs Hogan at March PPV (No Presidency on line) but Hogan (with NWO Help) retains.
Keep in mind I like the Finger Poke of Doom. Total swerve, no one saw it coming, it re-formed the real NWO, Killer heels, total anti authority, spitting on tradition, plus it set up the purge of all the midcarders who swelled the ranks and weakened the team throughout 98. Every company needs a lead heel/group and Hogan & NWO filled that void perfectly.
Now WCW did not have Sting (out till April), Hart (didnt wrestle full time till spring), Luger (returned in Sept), or Savage (returned in April) - all out injured yet leading into SuperBrawl they twice topped 5 ratings despite being in direct competition with RAW so interest in the reformed NWO, Flair & Goldberg was huge following Starrcade 98.
Moving into the spring & summer I would work the returning Hart and Sting into the NWO conflict but also with DDP, Jericho, & Eddie Guerrero. The US Title would c6e into play, with Hart or DDP holding the belt and defending against the others. Id also have Sting insert himself between Goldberg & Hogan, positioning himself as the next challenger after they done with each other.
Steiner was way over as a monster heel, Id have him & Bagwell dominate the tag title into the summer before branching off into singles feuds.
Id also have Bischoff obsessed with Flair, trying to get The Pres off him. After March vs Hogan Flair would turn back challenges from Hall & Henning (Id leave him NWO), setting up a big summer feud vs Nash. At GAB Goldberg beats Hogan & Horsemen win tag titles, a huge blow to the NWO. On Nitro Flair puts up Pres vs Nash (Bischoff leaves for good if Nash loses). Special guest ref Luger turns on WCW and screws Flair. Nash re enacts Fingerpoke the next week with Bischoff, making him Pres. Heading into Bash At Beach You have Flair-Nash & Hogan -Goldberg 3 (Steel Cage, No DQ). Nash cheats and goes over Flair but in the main event Flair saves Goldberg from major NWO rulebreaking and Hogan is defeated. Id have Hogan disappear after and be off TV. When Savage returns in the spring Id have him try to force Flair to give him favorable treatment to thank him for his NWO swerve that won Flair the Pres to begin with, make it a real source of contention, particularly with Sting angling into position to get GB-Hogan winner. Team Madness (Savage & Sid) cost Flair vs Nash, setting up a late summer-early fall lineup of Flair & H-Men battlhng Team Madness while Team Madness goes against Goldberg & Sting. Id get some use out of Steiner vs Hart here too and allign DDP with Goldberg (he needs a friend besides Flair). By Sept Id get ready for another NWO-WCW Wargames, with team NWO winning thanks to more shenanigans from Luger (1st appearance since June).
By Halloween Havoc GB needs some non NWO opposition, enter Brett Hart. Id let Steiner get the US title by now, maybe time for an E. Guerro face turn. Bischoff, still obsessed with Flair, puts a bounty on him, Jericho tries to collect. Hall & Nash feuding with DDP, Sting vs Luger, Henning & Bagwell tied up with Team Madness.
Id have Hogan return at the Nov PPV, saving a popular fave, disowning the NWO, setting up him vs Nash at Starrcade. Id have Savage vs Hart, Sting vs Steiner, DDP-Luger. Id also have Flair run the gauntlet, his career on line in each match, 3 matches chosen by Bischoff but if he wins 1st two (Bagwell & Sid) then Goldberg & the title await in main event. That would be my Starrcade.