Timeline: Spoilers from the episodes 1 & 2 + season 3 & 4 of TV show

I do not believe that the Telltale game will surpass the TV series in terms of time. This is because in the FAQ for the game we are told that "The events in our game series begin towards the end of Season Three of the TV show, and end right before the beginning of Season Five. You will visit familiar locations such as King’s Landing and The Wall, as well as unfamiliar locations such as Ironrath, the home of House Forrester."

The Battle of the Fist of the First men also takes place during 299 AC however this has little connection to the Telltale game as it has already occurred by the time that Gared reaches the wall (this is apperent as they have no Lord Commander). The battle was many men in the Night's Watch were massacred at the Fist of the First men by an attack from the Withers (or Othors) during an expedition by the Night's Watch north of the wall to find wildlings.

299 AC/300 AL

Red Wedding
This event takes place in the year 299 AC (After Conquest). The self-proclaimed 'King of the North' Robb Stark is murdered alongside most of his forces after attending the union of Edmure Tully and Roslin Frey at the Twins. During the festivities the Frey's along with the Boltons ambush the Stark's forces.
In Telltale universe:
Lord Forrester, his son Rodrik and his squire Gared Tutle were in attendance. House Forrester was serving House Stark at the time. Lord Forrester was murdered by Frey troops, Rodrik was believed to be dead by Gared (later found to be alive and returned to Ironwrath in the guise of a "dead body"). Gared Tutle survived and was able to deliver Lord Forrester's sword to Ironwrath and inform his uncle of a secret message given to him by Lord Forrester that "The North grove must not fall".
The Red Wedding formed the opening scene of the Telltale game.

Fall of Astapor
Daenerys Targaryen, claimant to the Iron throne of Westeros, arrived in Astapor to purchase an army of Unsullied soldiers. After exchanging one of her dragons (Drogon) for the army she then commanded the troops to liberate Astapor from the Good Masters leaving a council of three men to rule the city.
This takes place within the duration of episode 1 of the Telltale game despite not being experienced by the player

Battle of Yunkai
Daenerys Targaryen's forces march north to towards the coast city of Yunkai fighting against the Yunkish garrison, Stormcrows and Second Sonds within the city. After defeating the Yunkish Daenerys demands that the slaves of the city - which make up a large part of the city's economy - be freed, in exchange for this the Yunkish were allowed to remain in control of the city.
In Telltale universe.
Asher and his companion, Beskha, captured a former slave master attempting to flee Yunkai during the battle.
Three days after the battle they were offered 8,000 gold dragons for the release of the slave master. The Lost Legion later came to deliver this and ensure his release yet instead murdered the captive and attacked Asher and Beskha. Malcom then arrived to bring Asher back to Westeros.

300 AC/301 AL

The Purple Wedding
On the first day of the year King Joffrey and Margaery Tyrell wed. He was killed during the festivities of the wedding by Lady Olenna Tyrell. Sansa Lannister (née Stark) fled the scene and was widely accused of killing the king along with her husband Tyrion Lannister.
Not long after the wedding King Joffrey's heir, Tommen Baratheon, took his place as king of Westeros. Tommen and Margaery Tyrell entered into a Betrothal.
In Telltale universe
In episode 1 Margaery Tyrell's desk shows a map of the wedding seating arrangements and discussing with Sera how Mira and Sera will be seated right at the back of the wedding. Mira writes a number of letters concerning her wedding during episode 2. In the preview for episode 3, Tyrion Lannister says "enjoy the wedding" to Mira, suggesting that the wedding will take place during episode 3 (or 4). I believe that episode 3 will end soon after the death of King Joffrey.

Tyrion's Trail
Tyrion Lannister is tried for his part in murdering King Joffrey by Tywin Lannister, Mace Tyrell and Oberyn Martell. Through bribary, Queen Cersei was able to secure a number of witnesses to come forward to testify against Tyrion. Many accounts by such witnesses were exaggerated, inaccurate or not true. His father suggested to him that he would be able to be exiled to the wall, yet Tyrion chose to leave his fate in the hands of the Gods with a trial by combat.
In Telltale universe:
This will likely influence Mira's deal with Tyrion?

Winter comes
Winter arrives in Westeros. Petyr Baelish murders Lysa Arryn.

Daenerys arrives in Meereen
Daenerys sieges Meereen and declares herself the queen of the city. Her advisor Jorah Mormont is then exiled as a result of his betrayal to Daenerys by acting as a spy for Robert Baratheon.
In Telltale universe
In the preview for episode 3 Asher and his party are shown to confront Daenerys dragons.

Assault of Castle Black
The wildlings - lead by Mance Rayder - assault Castle Black. Stannis Baratheon, the legitimate heir to Robert Baratheon, arrives to defeat the wildlings with his army.
In Telltale universe
It is probable that Gard Tutle will participate/witness this.

Tyrion's Trail by Combat
Oberyn Martell offered to fight the Mountain for Tyrion in his trial. The final episode of season 4 ends with Oberyn Martell being killed by the Mountain.

If you would like to add anything else please say so in the comments - and discuss!

SPOILERS FROM BOOKS:
I wonder how Stannis' attack on the north will play out for the Forresters? In the books it is mentioned that the Forresters sent a scout to help him. Does this mean that we will have the option to stand with either Stannis or the Ramsey Snow? If so - who would you pick? (It is likely that such a choice will not be made until season 2)!