If you followed this post last year and matched from some other hotel status to Wyndham Diamond to Caesars Diamond, it’s time to match back from Caesars Diamond to Wyndham Diamond. While I matched to Wyndham Diamond last year, it was a temporary challenge. I did not complete the necessary nights and thus my status dropped to “Blue” (general member) in late summer. My Caesars status stuck as was expected (that status expires at the end of January). Today, I successfully matched Caesars Diamond back to Wydnham Diamond. On February 1st, I expect to be able to match back to Caesars Diamond again and hopefully leverage that for another $100 Diamond celebration dinner this year (which as Greg recently mentioned made for one of the most read posts on Frequent Miler in 2018) and free show tickets. If you currently have Caesar’s Diamond status, go here to match back to Wyndham Diamond now. Read on for the original post about how the match works and the updated step 6 section about matching back as outlined in this opening paragraph. H/T to Miles to Memories for the reminder to do this today.

Original post published in May 2019 followed by the newly added Step 6:

We recently posted both here on Frequent Miler and in our Frequent Miler Insiders Facebook group asking readers about topics they’d like to hear about. There were some awesome suggestions that I’m looking forward to covering. One topic that came up a couple of times was status matching. Today I’m not going to cover a complete guide to status matching, but rather a current opportunity to start from zero and end up with useful status in several programs with relative ease – and to possibly bring it full circle to even higher status than one started with.

Real-life motivation

While I’m covering this topic in response to some folks asking for posts on status matching, the particular path I’m outlining today was inspired by an upcoming trip with family. I’m heading to Las Vegas soon for a few days and we’ll be traveling with my sister-in-law and brother-in-law. We’ve recently dipped their toes in the miles-and-points pool, getting them set up late last year to earn the Southwest Companion Pass for 2019 and 2020. They did not yet have any hotel credit cards / points / status. We decided to do something heretical in order to better position them for our upcoming trip: my sister-in-law, henceforth referred to as “Sissy” for the purposes of this post, burned a 5/24 spot on the Hilton Honors Surpass card :-O.

Doing so bought her a ticket for the status match merry-go-round, or status-match-go-round if you will.

Why the Surpass?

The Hilton Honors Surpass card comes with automatic Hilton Gold status — good for free breakfast at most Hilton hotels and resorts and some extra points per dollar spent at Hilton. That’s a good deal for the $95 annual fee and leads some to question the value of Hilton Diamond (I’d still argue that the Amex Hilton Honors Aspire is well worth the money, but I’ll come back to why I had Sissy apply for the Surpass over the Aspire in a minutes). She used the link listed on our Best Offers page and set herself up to earn a nice haul of Hilton Honors points once she meets the minimum spending requirements.

A few reasons I suggested Sissy open the Surpass card:

  1. Sissy doesn’t have other hotel points, so she often pays for stays. This way, she’ll get free breakfast and some extra points on those paid stays.
  2. The Surpass card earns 6x at US Supermarkets, US restaurants, and US gas stations and she spends quite a bit in those categories.
  3. The Surpass earns a free weekend night after spending $15K in a calendar year. She’ll likely hit this requirement.
  4. To get on the status-match-go-round

I suggested she open the Surpass instead of the Aspire, despite my strong affinity for the Aspire card, for two reasons:

  1. Upgrade offers from the Surpass to Aspire are pretty common and sometimes as good as the new cardmember offer. She might be able to eventually snag two bonuses with one 5/24 slot.
  2. She might be able to get Hilton Diamond status without the Aspire card….

More on #2 to come in Step 4. But first, here are the steps she took to leverage status matches, starting with Hilton Gold from the Amex Hilton Surpass.

Step 1: Apply for the Surpass

Not much to say here — she applied and was approved for the Hilton Honors Surpass card instantly.

Step 2: Status match Hilton Gold to Wyndham Diamond

Wyndham has been offering a status match since last fall whereby they’ll match your status with another hotel chain (See: Wyndham Rewards Now Offering Status Match Up To Diamond Status). The interesting thing about the status match is that you don’t necessarily need top-tier status in another program to match to Wyndham’s top-tier Diamond status (this varies based on the program from which you match).

Specifically, reports have long indicated that Wyndham Rewards matches both Hilton Diamond and Hilton Gold to Wyndham Rewards Diamond status. Sissy signed up for a new…

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