When does TNG take place in relation to DS9?

Question

I've noticed character crossovers in each series but considering the timeline is mostly linear, when does TNG take place in relation to DS9?

As an example I've noticed a correlation in the Maquis and a mention of Cardassian occupation but I'm not aware as to when these took place in a linear timeline. Interactions of the two based on star dates, episodes, and also novels. I'd like to know the story behind these interactions etc..

Answer 1

Wikipedia shows the dates of the series as follows:

2364    TNG s1
2365    TNG s2
2366    TNG s3
2367    TNG s4
2368    TNG s5
2369    TNG s6          DS9 s1
2370    TNG s7          DS9 s2
2371    Generations     DS9 s3  VOY s1
2372                    DS9 s4  VOY s2
2373    First Contact   DS9 s5  VOY s3
2374                    DS9 s6  VOY s4
2375    Insurrection    DS9 s7  VOY s5
2376                            VOY s6
2377–78                         VOY s7
2379    Nemesis

Note, these are the main timelines of the shows, ignoring any time travel or flashbacks.

Answer 2

As noted, the overlap in the series' timelines is basically the same as the overlap in their air dates; DS9 begins after TNG Season 5, and TNG ends before DS9 Season 3. But here are a few events that anchor the timelines (spoilers for both series abound below):

2364 (TNG Season 1)

• The Enterprise-D makes its maiden voyage to Farpoint Station and encounters Q (TNG: Encounter at Farpoint).

2366 (TNG Season 3)

• The Enterprise encounters the Borg again; Picard is assimilated, becoming Locutus of Borg (TNG: The Best of Both Worlds, Part I)

2367 (TNG Season 4)

• The Federation engages the Borg in the Battle of Wolf 359. Benjamin Sisko takes part as first officer of the USS Saratoga, which is badly damaged; his wife Jennifer is killed (seen in flashback in DS9: Emissary). At length the Borg are turned away and Picard is recovered (TNG: The Best of Both Worlds, Part II).
• The Federation signs an armistice with the Cardassian Union, with which it had been at war for some time. However, skirmishes continue along the Federation-Cardassian border. Some inhabitants of Federation colonies that were ceded to the Cardassians, feeling betrayed by the Federation's choice of peace at the cost of their homes, form the resistance known as the Maquis (TNG: The Wounded).

2368 (TNG Season 5)

• The Federation colony Solarion IV is apparently attacked by Bajoran terrorists, and Bajoran Ensign Ro Laren joins the Enterprise as part of the investigation, staying on afterwards. This is our first exposure to Bajorans and the Cardassian occupation of Bajor (TNG: Ensign Ro).

2369 (TNG Season 6, DS9 Season 1)

• The Cardassians end their occupation of Bajor. The Federation takes over the abandoned outpost Terok Nor, renaming it Deep Space Nine, with Benjamin Sisko in command. The Enterprise and Picard pay a visit to the station, and Sisko blames Picard for his wife's death. Chief O'Brien transfers to DS9 from the Enterprise. The Bajoran wormhole is discovered and DS9 moves to the mouth of the wormhole (DS9: Emissary).
• Cardassian troops formerly stationed in the Bajoran sector are now probing the Federation border with apparently hostile intent (TNG: Chain of Command).
• The Enterprise again visits Deep Space Nine, and Worf learns more about his past and an outcast group of Klingons (TNG: Birthright).
• "Thomas" Riker, a transporter duplicate of William Riker trapped on the planet Nervala IV since 2361, is rescued by the Enterprise and continues his Starfleet career (TNG: Second Chances).

2370 (TNG Season 7, DS9 Season 2)

• Sent to infiltrate and spy on the Maquis, Ro Laren defects to them instead (TNG: Preemptive Strike).
• The Enterprise encounters Q again, Picard prevents a temporal anomaly, and sits down to a poker game with his officers. TNG ends (TNG: All Good Things...).

2371 (Generations, DS9 Season 3)

• After an encounter with Tolian Soran and the Nexus near Veridian III, the Enterprise-D is destroyed (Star Trek Generations).
• "Thomas" Riker visits DS9 in the guise of Will Riker and commandeers the Defiant, having joined the Maquis sometime since 2369 (DS9: Defiant).

2372 (DS9 Season 4)

• Facing Klingon-Cardassian hostilities, Starfleet dispatches Worf to Deep Space Nine, where he remains. (DS9: The Way of the Warrior).

2373 (First Contact, DS9 Season 5)

• The Borg launch an attack on Earth. The Enterprise-E happens to get there just in time to rescue Worf from the crippled Defiant (so that he can join the crew for this movie), then follow the Borg back in time (Star Trek: First Contact).

2375 (Insurrection, DS9 Season 7)

• Worf happens to be visiting the Enterprise on leave (so that he can join the crew for this movie) when it becomes embroiled in the Son'a-Ba'ku conflict (Star Trek: Insurrection).
• Dukat is up to no good, Sisko gets sucked up to the Celestial Temple, Kira becomes commander of DS9, Worf becomes the Federation Ambassador to the Klingon Empire, and the O'Briens return to Earth where Miles will teach at Starfleet Academy. DS9 ends. (DS9: What You Leave Behind).

2379 (Nemesis)

• Worf happens to be visiting the Enterprise for the marriage of Troi and Riker (so that he can join the crew for this movie) when the Enterprise investigates a bunch of contrived nonsense involving Romulans and clones (Star Trek: Nemesis). With the last movie featuring Picard & company, TNG as we know it ends.