As it has been since 2011, the Timbers Army led the national anthem and raised a tifo remembering the MLS Cup final victory with the words "Kiss.

In the 68th minute, Higuaín was able to control the ball that lightly bounced off of Taylor's back and finish with a bicycle kick to equalize Columbus Crew SC.

The Timbers answered in the 79th minute with a goal from Adi, who recovered the deflection from goalkeeper Steve Clark that blocked Asprilla's low shot.

The Timber's felt the loss of Liam Ridgewell who was ruled out with a hamstring injury shortly before the San Jose away match.

Jack Barmby was announced to join the Timbers on loan from Leicester City and Darren Mattocks was signed from Vancouver Whitecaps FC.

Despite playing against a 9-man Salt Lake squad, out-shooting them 26–7, and having 17 corners to their 4, the Timbers were unable to steal the victory and had to settle for the draw.

Chris Klute returned to the first team from Timbers 2, getting his first appearance as the squad continued to find a replacement for the left back position.

In the 74th minute, the Darlington Nagbe had to be carried off the pitch and return to the locker room via wheelchair due to a serious foul by Nigel de Jong to the ankle, who managed to escape with only a yellow card.

The Timbers continued their busy week, this time going against FC Dallas on a rainy Wednesday evening, 3 days after their draw with LA.

Darren Mattocks prevented FC Dallas' clean sheet by scoring in the 67th minute, giving him his first goal as a Timber player.

The Timbers played their 3rd and final match of the week, taking a victory at home against San Jose Earthquakes.

The Timbers would win it as the final goal was struck by Diego Valeri, which also happened to be his birthday that day, from a free kick around 22 yards out.

With the help of backup goalkeeper, Jake Gleeson, who made 4 amazing saves, the Timbers would take 3 points at home with a 2–1 win.

In extra time in the first half, the Timbers would lose Dairon Asprilla to a red card from an elbow to the face.

The Timbers entered the 102nd U.S. Open Cup at home against San Jose Earthquakes, who the team recently defeated at the start of the month in regular MLS season play.

Diego Valeri would return from his injury and capture a brace in the 44th and 50th minute with one being assisted by Lucas Melano and the other by Jermaine Taylor.

The Timbers were table to hold the score 0–0 at the half, but a goal from Jacob Peterson off of a free kick from Benny Feilhaber.

The Timbers would take another loss as they prepare for CONCACAF Champions League Group play starting mid week.

Near the end of the match, Jack Jewsbury would score a howler in the 87th minute from a burdened Darlington Nagbe who was able to complete the pass having dealt with two defenders attacking him.

Fanendo Adi, who did not start due to a report of the player missing the team plane as punishment, was able to score the last goal and prevent a shut out from Seattle in added time.

For the final time during regular season play, the Timbers went against their main rivals, Seattle Sounders at home.

The ball took a deflection off an attempted save from Stefan Frei, hitting the top crossbar, and crossed the line before rolling back out.

The 2nd goal was in the 29th minute by Fanendo Adi from a saved shot from Diego Valeri and send the ball into the back of the net.

On September 10, the Timbers hosted Real Salt Lake in a crucial match that would keep them fully in control of their playoff fate.

Playing their first CONCACAF Champions league away match of the year, the Timbers traveled to Costa Rica to take on Deportivo Saprissa.

On September 18, Jack Jewsbury, the first Timbers captain of their MLS era, announced he would retire at the end of the 2016 season.

The match went scoreless during the first half, however at the start of the second, Diego Valeri put the ball in the back of the net in the 46th minute, assisted by Darren Mattocks.

The Timbers traveled to their final away match in CCL group stage play to face Club Deportivo Dragón in El Salvador.

As the regular season begins to come to a close and still chasing a playoff spot, the Timbers traveled to Commerce City to face Colorado Rapids.

The match would prove to be a disaster as the Timbers only scored a single goal off a penalty taken and converted by Diego Valeri in the 72nd minute.